N-(tert-butoxycarbonyl)glycine → Boc-Gly-Leu-Ala-OBzl

HRID 4983

Reaction equation

HRID 4983 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.[NH2:13][C@H:14]([C:19]([NH:21][C@H:22]([C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])[CH3:23])=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17]>>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:13][C@H:14]([C:19]([NH:21][C@H:22]([C:24]([O:26][CH2:27][C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1)=[O:25])[CH3:23])=[O:20])[CH2:15][CH:16]([CH3:17])[CH3:18])=[O:5]

Participants

3

Reactant 2

HCID 78288N-(tert-butoxycarbonyl)glycineHCID 16742166H-Leu-Ala-OBzl

Product 1

HCID 131717744Boc-Gly-Leu-Ala-OBzl

Procedure

Boc-Gly-Leu-Ala-OBzl was prepared by coupling Boc-Gly-OH (5.70 g, 32.6 mmoles) to H-Leu-Ala-OBzl using the mixed anhydride procedure described in Example 2. The product (13.8 g) was obtained as an amorphous solid. Boc-Gly-Leu-Ala-OBzl was deblocked with trifluoroacetic acid by the procedure described for the preparation of H-Leu-Ala-OBzl except that the trifluoroacetate salt was soluble in ether. The preparation was dissolved in ethyl acetate and treated with anhydrous hydrogen chloride. The resulting product was precipitated by the addition of ether to yield 7.7 g of H-Gly-Leu-Ala-OBzl HCl in a first crop.

Sources & evidence

ORD record
ord-e95bb68602144d5c8b548570c446fb1d
Source dataset
uspto-grants-1993_09
Patent number
US05242904

Linked notes

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