4-Nitrobenzyl chloroformate → HCID 54015813, compound

HRID 375737Notes

Reaction equation

[OH:1][C@@H:2]([CH3:11])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1)=[O:14]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[N+:23]([C:20]1[CH:19]=[CH:18][C:17]([CH2:16][O:15][C:13]([O:1][C@@H:2]([CH3:11])[CH2:3][C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[O:14])=[CH:22][CH:21]=1)([O-:25])=[O:24]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3.84 g of tert-butyl (S)-3-hydroxybutyrate and 5.86 g of 4-dimethylaminopyridine in 20 ml of methylene chloride was added at 0° C. within 20 minutes a solution of 6.47 g of p-nitrobenzyl chloroformate in 20 ml of methylene chloride. The mixture was stirred for 3 hours at 0° C., then diluted with 50 ml of methylene chloride and washed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution, and with brine. The organic layer was dried over sodium sulfate, and the solvent was evaporated in vacuo. The residual oil was chromatographed on silica gel using ethyl acetate/hexane (1:1, v/v) as eluent to yield 5.10 g of tert-butyl (S)-3-(4-nitrobenzyloxycarbonyloxy)-butyrate as a colourless oil.

Workup

washwashed successively with 1N hydrochloric acid, saturated sodium bicarbonate solution
dry with materialThe organic layer was dried over sodium sulfate
customthe solvent was evaporated in vacuo
customThe residual oil was chromatographed on silica gel

Sources & evidence

ORD record: ord-e8e486a225e6400c9ff3ca67ee009af2
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05486466

Reaction notes

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