HCID 24730374, compound → HCID 67081010, compound

HRID 655523Notes

Reaction equation

HRID 655523 reaction equation
N[C@H](CCC1C=CC=CC=1)CO.[C:13]([O:17][C:18](=[O:44])[N:19]([CH2:31][CH2:32][C:33](=[O:43])[NH:34]OCC1C=CC=CC=1)[C@H:20]([CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:21]O)([CH3:16])([CH3:15])[CH3:14].C(OC(N1CCC(=O)N(OCC2C=CC=CC=2)C[C@H]1CCC1C=CC=CC=1)=O)(C)(C)C>>[C:13]([O:17][C:18]([N:19]1[CH2:31][CH2:32][C:33](=[O:43])[NH:34][CH2:21][C@H:20]1[CH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:44])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 24730374HCID 24730374, compoundHCID 67080841HCID 67080841, compoundHCID 86638110HCID 86638110, compound

Product 1

HCID 67081010HCID 67081010, compound

Procedure

The title compound, m/e=444.3, was produced in analogy with intermediate 16, steps A to D. Thus, (R)-2-amino-4-phenylbutan-1-ol was elaborated to (2-benzyloxycarbamoyl-ethyl)-((R)-2-hydroxy-1-phenethyl-ethyl)-carbamic acid tert-butyl ester in step A, then cyclized in step B, leading to (R)-4-benzyloxy-5-oxo-2-phenethyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester. Hydrogenation in step C gave (R)-5-oxo-2-phenethyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester, which was alkylated with 1-(3-chloropropyl)piperidine in step D.

Sources & evidence

ORD record
ord-d7913ea1186e4845aeb13ca7caa3c5da
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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