Boc-L-phenylalanine methyl ester → Methyl 2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoate

HRID 847304Notes

Reaction equation

HRID 847304 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]>[Rh]>[C:9]([O:8][C:6]([NH:5][CH:4]([CH2:13][CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1)[C:3]([O:2][CH3:1])=[O:20])=[O:7])([CH3:12])([CH3:10])[CH3:11]

Participants

3

Reactant 1

HCID 9882138Boc-L-phenylalanine methyl ester

Product 1

HCID 4264602Methyl 2-((tert-butoxycarbonyl)amino)-3-cyclohexylpropanoateYield 86,316.102%

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

315.3 g (1.28 mmol) of t-butoxycarbonyl-L-phenylalanine methyl ester are hydrogenated in the presence of 5% rhodium on aluminium oxide at room temperature and 440 kPa according to the method described by J. Boger et al. in J. Med. Chem., 28, 1779 (1985), whereby there are obtained 315.3 g of methyl 2-t-butoxycarbonylamino-3-cyclohexylpropionate as an oil which is used directly in the next step.

Sources & evidence

ORD record
ord-b3fce082b7f0409c9832077b90ae6aca
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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