Benzyl chloroformate → N-carbobenzyloxy-beta-chloro-L-alanine

HRID 430013Notes

Reaction equation

[Cl:1][CH2:2][C@@H:3]([C:5]([OH:7])=[O:6])[NH2:4].[CH2:8]([O:15][C:16](Cl)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[OH-].[Na+]>>[CH2:8]([O:15][C:16]([NH:4][C@H:3]([C:5]([OH:7])=[O:6])[CH2:2][Cl:1])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 14798Sodium Hydroxide

HCID 4397723-chloro-L-alanine

Product 1

HCID 11043414N-carbobenzyloxy-beta-chloro-L-alanineYield 100%

Conditions

Temperature: 5 °C

Procedure

To 86.19 g of an aqueous solution containing 7.47 g of β-chloroalanine was added 11.35 g of benzyloxycarbonyl chloride (1.1 moles per mole of β-chloroalanine) dropwise over 1 hour under constant stirring at about 5° C., with the reaction system being maintained at pH 9.7 with a 30% aqueous solution of sodium hydroxide. The reaction was further continued for 3 hours, at the end of which time the reaction mixture was washed with 50 ml of toluene. This washed reaction mixture, 89.53 g, contained 15.52 g (yield 100%) of N-benzyloxycarbonyl-β-chloroalanine.

Workup

washthe reaction mixture was washed with 50 ml of toluene
customThis washed reaction mixture, 89.53 g

Sources & evidence

ORD record: ord-9e171b00618d431f8a5c72a6dfc94b1b
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06320072B1

Reaction notes

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