N-Methylbenzylamine → tert-Butyl{(1R)-1-[benzyl(methyl)carbamoyl]-3-phenylpropyl}carbamate

HRID 537396Notes

Reaction equation

[C:1]([NH:8][C@@H:9]([C:18]([OH:20])=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:21][NH:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(OC(=O)NC(C(N1CCC(C)CC1)=O)CCC1C=CC=CC=1Cl)(C)(C)C>>[C:4]([O:3][C:1](=[O:2])[NH:8][C@@H:9]([C:18](=[O:20])[N:22]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:21])[CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([CH3:5])([CH3:6])[CH3:7]

Participants

Reactant 3

HCID 7669N-Methylbenzylamine

HCID 2755954Boc-D-homophenylalanine

HCID 131731949Tert-butyl{3-(2-chlorophenyl)-1-[(4-methylpiperidin-1-yl)carbonyl]propyl}carbamate

Product 1

HCID 91008624tert-Butyl{(1R)-1-[benzyl(methyl)carbamoyl]-3-phenylpropyl}carbamate

Procedure

tert-Butyl{(1R)-1-[benzyl(methyl)carbamoyl]-3-phenylpropyl}carbamate is prepared from Boc-(D)-homophenylalanine and N-methylbenzylamine in the same manner that tert-butyl{3-(2-chlorophenyl)-1-[(4-methylpiperidin-1-yl)carbonyl]propyl}carbamate is synthesized.

Workup

customis synthesized

Sources & evidence

ORD record: ord-035cdb81f8654fce985440edd280cf6c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859814B2

Reaction notes

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