1-Acetoxy-2-bromoethane → HCID 76489103, compound

HRID 1953918Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([NH:24][C:25](=[O:33])[CH:26]([NH:31][CH3:32])[CH2:27][CH:28]([CH3:30])[CH3:29])[C:17](=[O:23])[NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:43]([O:46][CH2:47][CH2:48]Br)(=[O:45])[CH3:44]>C1COCC1>[CH2:47]([O:46][C:43](=[O:45])[CH2:44][N:31]([CH:26]([C:25](=[O:33])[NH:24][CH:16]([C:17](=[O:23])[NH:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1)[CH2:27][CH:28]([CH3:30])[CH3:29])[CH3:32])[CH3:48]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of [S-(R*,R*)]-4-methyl-2-methylamino-pentanoic acid [2-(4-benzyloxy-phenyl)-1-tert-butylcarbamoyl-ethyl]-amide (0.55 mmol), diisopropyl ethylamine (1.65 mmol), 2-bromoethyl acetate (0.8 mmol), and anhydrous THF (6 mL) was stirred at 25° C. for 6 hours. The precipitate was filtered off. The reaction mixture was concentrated and purified by column chromatography on silica gel eluting with 10% acetone/methylene chloride to give the titled compound (84% yield).

Workup

filtrationThe precipitate was filtered off
concentrationThe reaction mixture was concentrated
custompurified by column chromatography on silica gel eluting with 10% acetone/methylene chloride

Sources & evidence

ORD record: ord-e45780fdc5714ac9818e8dacf74a05cf
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06117841

Reaction notes

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