A novel protocol for N-methyl-γ-amino-β-hydroxy acids from oxazolidinones

Abstract

A new two step methodology for N-methyl-γ-amino-β- hydroxy acids from oxazolidinones is described

References

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9. Selected data for 2a: Colorless syrup; δ_H 1.30 (3H, t, J 6.4, CH₂CH₃), 3.00–3.40 (2H, m, PhCH₂), 4.20 (2H, q, J 6.4, CH₂CH₃), 4.80–4.90 (1H, m, CHBn), 5.05 (2H, s, PhCH₂O), 5.20–5.32 (1H, br s, N-CH₂), 5.35 (1H, s, olefin), 5.60 (1H, br s, N-CH₂), 7.00–7.40 (10H, m, Ar); δ_C 14.3 (C-9), 38.7 (CH₂Ph), 59.5 (C-8), 59.8 (C-4), 67.7 (C-11), 91.0 (C-2), 126.7 (Ar), 128.0 (Ar), 128.2 (Ar), 128.3 (Ar), 128.6 (Ar), 129.7 (Ar), 130.5 (Ar), 132.5 (Ar), 136.3 (C-6), 154.2 (C-10), 167.1 (C-5), 171.5 (C-7); m/z 382 (M⁺+ H). For 2b: Colorless syrup; δ_H 0.82 (3H, d, J 6.7, CH₃), 1.00 (3H, d, J 6.7, CH₃), 1.22 (3H, t, J 6.2, CH₂CH₃), 1.30–1.80 (3H, m), 4.10 (2H, q, J 6.2, CH₂CH₃), 4.90 (1H, d, J 4.5), 5.12 (2H, ABq, J_gem 13.5, CH₂Ph), 5.22 (1-H, s, olefin), 5.50 (1H, br s, N-CH₂), 5.65 (1H, br s, N-CH₂), 7.30 (5H, m, Ar); δ_C 14.2 (C-9), 20.8 (CH₃), 23.5 (CH₃), 24.9 (CH₂), 39.9 (CH), 57.6 (C-8), 59.4 (C-4), 67.9 (C-11), 89.9 (C-2), 128.2 (Ar), 128.4 (Ar), 135.4 (C-6), 154.0 (C-10), 166.6 (C-5), 172.1 (C-7); m/z 348(M⁺+ H). For 2c: Colorless syrup; δ_H 0.88 (3H, t, J 6.2, CH₃CH₂), 1.20 (3H, d, J 6.8, CH₃), 1.28 (3H, t, J 6.2, CH₂CH₃), 1.30–1.50 (2H, m, CH₂CH₃), 2.00–2.20 (1H, m, CH(CH₃)CH₂CH₃), 4.10 (2H, q, J 6.2, CH₂CH₃), 4.92 (1H, d, J 4.6, N-CH), 5.15 (2H, ABq, J_gem 14.0, OCH₂Ph), 5.30 (1H, s, olefin), 5.40 (1H, br s, N-CH₂), 5.62 (1H, br s, N-CH₂), 7.30 (5H, m, Ar); δ_C 11.7 (CH₃), 14.0 (C-9), 16.2 (CH₃), 23.6 (CH₂), 39.1 (CH), 59.3 (C-8), 63.9 (C-4), 67.7 (C-11), 90.6 (C-2), 128.0 (Ar), 128.1 (Ar), 128.2 (Ar), 135.4 (C-6), 154.2 (C-10), 166.6 (C-5), 171.4 (C-7); m/z 348 (M⁺+ H). For 3a: Colorless syrup; [α]²⁵_D– 29.4, (c 1, MeOH); δ_H 1.25 (t, 3H, CH₃), 2.40–2.55 (m, 2H, CH₂Ph), 2.80 (s, 3H, N-CH₃), 2.95–3.10 (m, 2H, CH₂CO₂), 4.00–4.18 (quartet overlapped with multiplet, 4H, CH₂CH₃ and CHNH and CHOH), 4.90–5.20 (m, 2H, PhCH₂O), 7.05–7.35 (m, 10H, Ar); δ_C 14.1, 30.6, 39.4, 58.6, 59.2, 59.9, 69.8, 79.2, 126.2, 128.2, 128.5, 128.7, 129.5, 130.2, 132.3, 154.4, 171.4; m/z 386 (M⁺+ H). For 4a: Colorless syrup; [α]²⁵_D–26.6 (c 1, MeOH); δ_H 1.20 (t, 3H, CH₃), 2.30–2.45 (m, 2H, CH₂Ph), 2.75 (s, 3H, N-CH₃), 3.00–3.20 (m, 2H, CH₂CO₂), 4.00–4.20 (quartet overlapped with multiplet, 4H, CH₂CH₃ and CHNH and CHOH), 5.00–5.15 (m, 2H, PhCH₂O), 7.10–7.35 (m, 10H, Ar); m/z 386 (M⁺+ H). For 7: Colorless oil; [α]²⁵_D–43.7 (c 1, CHCl₃); lit.^4c[α]²⁵_D–41.2 (c 1, CHCl₃); δ_H 0.09 (s, 3H, Si-CH₃), 0.20 (s, 3H, CH₃-Si), 0.95 (s, 9H, (CH₃)₃C-Si), 1.35 (s, 9H, (CH₃)₃C), 2.35–2.50 (m, 2H, CH₂Ph), 2.75 (s, 3H, N-CH₃), 2.90–3.05 (m, 2H, CH₂CO₂), 4.25–4.40 (m, 2H, CH-NH and CH-OH), 7.10–7.35 (m, 5H, Ph); δ_C–4.7, –4.6, 14.2, 18.3, 25.6, 30.5, 35.7, 39.9, 56.2, 60.9, 71.1, 76.9, 79.2, 126.3, 128.0, 129.2, 138.7, 155.0, 171.5; m/z 324 (M⁺+ H)..