Benzyl chloroformate → CBZ-L-ALANINOL

HRID 2294307Notes

Reaction equation

HRID 2294307 reaction equation
[NH2:1][C@H:2]([CH2:4][OH:5])[CH3:3].[CH2:6]([O:13][C:14](Cl)=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C.O1CCCC1>[CH2:6]([O:13][C:14]([NH:1][C@@H:2]([CH3:3])[CH2:4][OH:5])=[O:15])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 2

HCID 10387Benzyl chloroformateHCID 80307L-Alaninol

Product 1

HCID 10262499CBZ-L-ALANINOL

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A procedure similar to that described in Preparation 7 was repeated, except that 14.55 g of L-alaninol, 126 ml of a 30-35% w/v solution of benzyloxycarbonyl chloride in toluene, 29.6 ml of triethylamine and 100 ml of anhydrous tetrahydrofuran were used, to give 8.15 g of the title compound, melting at 79° C. to 80° C.

Workup

  1. customA procedure similar to that described in Preparation 7

Sources & evidence

ORD record
ord-2d34b132229743b59ec82e0219840814
Source dataset
uspto-grants-1997_11
Patent number
US05688823

Reaction notes

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