N-Boc-O-benzylserine hydroxysuccinimide → Methyl o-benzyl-n-(tert-butoxycarbonyl)serinate

HRID 37040Notes

Reaction equation

[C:1]([NH:8][C@H:9]([C:19]([OH:21])=[O:20])[CH2:10][O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[CH:23]1CC(=O)NC1=O>CO>[CH3:23][O:20][C:19](=[O:21])[C@H:9]([CH2:10][O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[NH:8][C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

Conditions

Temperature: 50 °C

Procedure

N-Boc-O-benzylserine-hydroxysuccinimide (16.0 g, 40.8 mmol) was dissolved in methanol (300 ml) and stirred at 50° C. for 24 hours. The solvent was evaporated and the residue was taken up in ethyl acetate (120 ml), washed with aqueous saturated sodium bicarbonate (2×50 ml) and water (50 ml). The organic solution was dried with sodium sulphate and after evaporation of the solvent the N-Boc-O-benzylserine methyl ester was isolated as a colourless oil. Yield 9.9 g (83%). The structure was confirmed by 1HNMR and 13CNMR.

Workup

customThe solvent was evaporated
washwashed with aqueous saturated sodium bicarbonate (2×50 ml) and water (50 ml)
dry with materialThe organic solution was dried with sodium sulphate
customafter evaporation of the solvent the N-Boc-O-benzylserine methyl ester
customwas isolated as a colourless oil

Sources & evidence

ORD record: ord-be50efe8dfe54b099a4f120eb3ffdd62
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05419893

Reaction notes

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