Triethylamine → 5-phenylpentyl-N-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate

HRID 530532Notes

Reaction equation

O[C@@H:2]([CH3:23])[C@@H:3]([N:7]([CH3:22])[C:8]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:9])[C:4]([OH:6])=[O:5].CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>C(Cl)Cl>[C:16]1([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][O:10][C:8](=[O:9])[N:7]([CH3:22])[C@H:3]2[C:4](=[O:6])[O:5][C@H:2]2[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of (2R,3S)-3-hydroxy-2-[methyl-(5-phenylpentoxycarbonyl)-amino]-butanoic acid (0.04 g, 0.14 mmol) in dry CH2Cl2(5.0 mL), under nitrogen atmosphere at 0° C., Et3N (0.06 mL, 0.41 mmol) and subsequently TBTU (0.05 g, 0.17 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. Upon full conversion of the starting material, the organics were removed under reduced pressure, and the resulting crude product absorbed over silica gel and purified by column chromatography, eluting with Cy:EtOAc (from 100:0 to 0:100) to afford the title compound (0.01 g, 23%), as a mixture of two rotamers (1:1.5 ratio), as a colorless oil. [α]25D −16.66 (c 0.1, CHCl3). 1H NMR (DMSO-d6) δ 1.29-1.41 (m, 10H), 1.53-1.69 (m, 8H), 2.58 (t, J=7.6 Hz, 4H), 2.93 (s, 6H), 3.98-4.11 (m, 4H), 4.77-4.89 (m, 2H), 5.24-5.33 (m, 1H, major rotamer), 5.35-5.43 (m, 1H, minor rotamer), 7.13-7.32 (m, 10H).

Workup

waitThe mixture was left
customUpon full conversion of the starting material, the organics were removed under reduced pressure
customthe resulting crude product absorbed over silica gel
custompurified by column chromatography
washeluting with Cy

Sources & evidence

ORD record: ord-884e41c8730540169c11338bb228b64b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353075B2

Reaction notes

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