Triethylamine → HCID 57523549, compound

HRID 530477Notes

Reaction equation

CCN(CC)CC.O[C@@H:9]([CH3:29])[C@@H:10]([NH:14][C:15]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:16])[C:11]([OH:13])=[O:12]>C(Cl)Cl>[C:23]1([CH2:22][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[CH3:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

In a two necked round bottom flask, Et3N (0.34 ml, 2.42 mmol) was added to a solution of (2R,3S)-3-hydroxy-2-({[(5-phenylpentyl)oxy]carbonyl}amino)-butanoic acid (0.25 g, 0.81 mmol) in dry CH2Cl2 (10 mL) under argon. After cooling at 0° C., HTBU (0.46 g, 1.21 mmol) was added and the mixture stirred 3 h at 0° C., then 16 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 98:2 to 80:20). The title compound (0.107 g, 45%), was obtained as white solid, which was further triturated with cyclohexane. MS (ESI) m/z: 290.21 [M−H]−. FTIR (cm−1): 3330, 3064, 3027, 2936, 2858, 1849, 1695, 1540, 1387, 1333, 1262, 1129, 1076, 1023, 985, 921, 845, 822, 741, 697. 1H NMR (CDCl3): δ 1.38 (m, 2H); 1.44 (d, 3H); 1.62-1.67 (m, 4H); 2.62 (t, 2H); 4.05-4.13 (m, 2H); 4.86 (m, 1H); 5.44 (t, 1H); 5.33 (d, 1H); 7.16-7.19 (m, 3H); 7.25-7.29 (m, 2H).

Workup

additionHTBU (0.46 g, 1.21 mmol) was added
custom16 h
customat rt
customthe solvent removed under vacuum
customThe crude was purified by typical silica gel column chromatography
washeluting with Cy/AcOEt (from 98:2 to 80:20)

Sources & evidence

ORD record: ord-c257130fd97f407baa1f2c770715516b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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