Triethylamine → HCID 73294497, compound

HRID 530474Notes

Reaction equation

CCN(CC)CC.O[C@@H:9]([CH3:28])[C@@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:16])[C:11]([OH:13])=[O:12].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[C:22]1([CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:15](=[O:16])[NH:14][C@H:10]2[C:11](=[O:13])[O:12][C@H:9]2[CH3:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a four necked round bottom flask, Et3N (5.5 mL, 39.4 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-{[(4-phenylbutoxy)carbonyl]amino}butanoic acid (3.9 g, 13.1 mmol) in dry CH2Cl2 (170 mL) under argon. After cooling at 0° C., HBTU (7.5 g, 19.7 mmol) was added and the mixture stirred 3 h at 0° C., then 3.5 h at rt. The obtained solid was filtered-off and the solvent removed under vacuum. The crude was purified by typical silica gel automatic column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting pale yellow oil (0.61 g) was further crystallized from cyclohexane to afford the pure title compound, (0.23 g, 6%), as white solid. MS (ESI) m/z: 276.24 [M−H]−. FTIR (cm−1): 3312, 3060, 3026, 2942, 2861, 1826, 1694, 1545, 1337, 1269, 1126, 1023. 1H NMR (CDCl3): δ 1.45 (d, 3H); 1.66-1.70 (m, 4H); 2.63-2.66 (m, 2H); 4.09-4.18 (m, 2H); 4.83-4.89 (m, 1H); 5.36 (br d, 1H); 5.45 (m, 1H); 7.16-7.31 (m, 5H).

Workup

custom3.5 h
customat rt
customthe solvent removed under vacuum
customThe crude was purified by typical silica gel automatic column chromatography
washeluting with Cy/AcOEt (from 95:5 to 60:40)
customThe resulting pale yellow oil (0.61 g) was further crystallized from cyclohexane

Sources & evidence

ORD record: ord-25e692c992894795903856411a48547b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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