Triethylamine → [(S)-1-(6-Bromo-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl)-ethyl]-methyl-carbamic acid benzyl ester

HRID 556269Notes

Reaction equation

[CH2:1]([O:8][C:9]([N:11]([CH3:17])[C@@H:12]([CH3:16])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:18][C:19]1[C:20](=[O:26])[NH:21][C:22]([Br:25])=[CH:23][CH:24]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([C@H:12]([C:13](=[O:15])[NH:18][C:19]1[C:20](=[O:26])[NH:21][C:22]([Br:25])=[CH:23][CH:24]=1)[CH3:16])[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-2-(benzyloxycarbonyl-methyl-amino)-propionic acid (2.7 g, 11.4 mmol) in 10 mL of CH2Cl2 at 0° C., is added 1-chloro-N,N-2-trimethyl-1-propenylamine (1.5 g, 11.4 mmol) drop wise. After being stirred at 0° C. for 20 minutes, the solution is added to a solution of 3-amino-6-bromo-1H-pyridin-2-one (1B) (1.8 g, 9.5 mmol) in 40 mL of CH2Cl2 at 0° C. slowly. Triethyl amine (3.2 ml, 22.8 mmol) is then added slowly. The reaction mixture is stirred at 0° C. for 1 hour, then washed with 2×15 ml of water, and concentrated. The crude product is purified by chromatography (CH2Cl2 95%, MeOH 5%) to give [(S)-1-(6-bromo-2-oxo-1,2-dihydro-pyridin-3-ylcarbamoyl)-ethyl]-methyl-carbamic acid benzyl ester (1C) (3.0 g, yield 79%) as purple solid. MS (ESI) m/e 408, 410 (M+H+).

Workup

stirringThe reaction mixture is stirred at 0° C. for 1 hour
washwashed with 2×15 ml of water
concentrationconcentrated
customThe crude product is purified by chromatography (CH2Cl2 95%, MeOH 5%)

Sources & evidence

ORD record: ord-f2228c91aa474066af88430ac4732323
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08058272B2

Reaction notes

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