4-Methylmorpholine → N-(tert-Butoxycarbonyl)-3-tert-butyl-D-alanyl-3-tert-butyl-L-alanine benzyl ester

HRID 2220817Notes

Reaction equation

HRID 2220817 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:15]([OH:17])=O)[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[C:19]([CH2:23][C@@H:24]([C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])[NH2:25])([CH3:22])([CH3:21])[CH3:20].CN1CCOCC1>>[CH2:29]([O:28][C:26](=[O:27])[C@H:24]([CH2:23][C:19]([CH3:21])([CH3:20])[CH3:22])[NH:25][C:15](=[O:17])[C@@H:9]([CH2:10][C:11]([CH3:12])([CH3:13])[CH3:14])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 3

HCID 79724-MethylmorpholineHCID 7021114(R)-2-((tert-Butoxycarbonyl)amino)-4,4-dimethylpentanoic acidHCID 68803323L-Leucine, 4-methyl-, phenylmethyl ester, hydrochloride (9CI)

Product 1

HCID 59709871N-(tert-Butoxycarbonyl)-3-tert-butyl-D-alanyl-3-tert-butyl-L-alanine benzyl esterYield 97%

Procedure

N-(tert-Butoxycarbonyl)-3-tert-butyl-D-alanine (3.28 g, 13.4 mmol) and benzyl 3-tert-butyl-L-alaninate hydrochloride (4.0 g, 14.7 mmol; J. X. He, W. L. Cody, A. M. Doherty, J. Org. Chem. 1995, 60, 8262-8266) are reacted by general procedure 6 (in this case 5 equivalents of N-methylmorpholine). Aqueous workup results in 6.0 g of product (97% of theory). The product can be finally purified by preparative HPLC (method 16).

Sources & evidence

ORD record
ord-1b17a3a6800b4284b9982d0c4a6ad9d1
Source dataset
uspto-grants-2008_05
Patent number
US07368424B2

Reaction notes

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