tert-Butoxycarbonyl-D-leucine → Benzyl n-(tert-butoxycarbonyl)-d-leucyl-3-tert-butyl-l-alaninate

HRID 2220814Notes

Reaction equation

HRID 2220814 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:18]([O:25][C:26](=[O:34])[C@H:27]([CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])[NH2:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:14]([NH:28][C@H:27]([C:26]([O:25][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:34])[CH2:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 637604tert-Butoxycarbonyl-D-leucineHCID 68803323L-Leucine, 4-methyl-, phenylmethyl ester, hydrochloride (9CI)

Product 1

HCID 59709729Benzyl n-(tert-butoxycarbonyl)-d-leucyl-3-tert-butyl-l-alaninate

Procedure

N-(tert-Butoxycarbonyl)-D-leucine (230 mg, 1.0 mmol) and benzyl-3-tert-butyl-L-alaninate hydrochloride (300 mg, 1.10 mmol) (John X. He, Wayne L. Cody, Annette M. Doherty, J. Org. Chem., 1995, 60, 8262-8266) are reacted by general procedure 6. The crude product is purified (workup method 2) by preparative HPLC (method 16), resulting in 362 mg (80% of theory) of product.

Workup

  1. customThe crude product is purified (workup method 2) by preparative HPLC (method 16)
  2. customresulting in 362 mg (80% of theory) of product

Sources & evidence

ORD record
ord-0bbb223aea8442d887cc74085e9313cd
Source dataset
uspto-grants-2008_05
Patent number
US07368424B2

Reaction notes

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