Triethylamine → HCID 86699910, compound

HRID 530469Notes

Reaction equation

CCN(CC)CC.O[C@@H:9]([CH3:27])[C@@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=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>[CH3:27][C@H:9]1[C@@H:10]([NH:14][C:15](=[O:16])[O:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:11](=[O:13])[O:12]1

Participants

Conditions

Temperature: 0 °C

Procedure

In a four necked round bottom flask, Et3N (7.3 mL, 52.5 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-({[2-(4-methylphenyl)ethoxy]carbonyl}amino) butanoic acid (4.85 g, 17.5 mmol) in dry CH2Cl2 (190 mL) under argon. After cooling at 0° C., HBTU (9.87 g, 26.2 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 column chromatography, eluting with Cy/AcOEt (from 95:5 to 60:40). The resulting white solid (0.658 g) was further triturated with cyclohexane to afford the pure title compound (0.450 g, 10%), as white solid. MS (ESI) m/z: 262.21 [M−H]−. FTIR (cm−1): 3299, 3050, 2966, 2924, 2854, 1827, 1690, 1540, 1355, 1270, 1121, 1095, 1021, 844, 817. 1H-NMR (CDCl3): δ 1.42 (d, 3H); 2.33 (s, 3H); 2.90 (t, 2H); 4.31 (t, 2H); 4.81-4.88 (m, 1H); 5.39-5.46 (m, 2H); 7.08-7.13 (m, 4H).

Workup

custom3.5 h
customat rt
customthe solvent removed under vacuum
customThe crude was purified by typical silica gel column chromatography
washeluting with Cy/AcOEt (from 95:5 to 60:40)
customThe resulting white solid (0.658 g) was further triturated with cyclohexane

Sources & evidence

ORD record: ord-b06eb044451a45b297c486d7130405eb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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