3-Azidobenzoyl chloride → {3-[3-(3-Azido-phenyl)-3-oxo-propionylamino]-biphenyl-4-yl}-carbamic acid tert.-butyl ester

HRID 1062039Notes

Reaction equation

HRID 1062039 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][C:9]=1[NH2:20])([CH3:4])([CH3:3])[CH3:2].C([O:24][C:25](=O)[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]=[N+:36]=[N-:37])[CH:30]=1)=[O:28])C.N(C1C=C(C=CC=1)C(Cl)=O)=[N+]=[N-]>>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10][C:9]=1[NH:20][C:25](=[O:24])[CH2:26][C:27]([C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N:35]=[N+:36]=[N-:37])[CH:30]=1)=[O:28])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 222247833-Azidobenzoyl chlorideHCID 57717454N-(3-Amino[1,1'-biphenyl]-4-yl)-carbamic Acid tert-Butyl EsterHCID 86587996HCID 86587996, compound

Product 1

HCID 86587995{3-[3-(3-Azido-phenyl)-3-oxo-propionylamino]-biphenyl-4-yl}-carbamic acid tert.-butyl ester

Procedure

Prepared (3-amino-biphenyl-4-yl)-carbamic acid tert.-butyl ester (Example G9) (569 mg, 2 mmol) and 3-(3-azido-phenyl)-3-oxo-propionic acid ethyl ester (700 mg, 3 mmol; prepared from 3-azido-benzoyl chloride (Bioorg. Chem 1986, 134) using the procedure described in Synthesis, 1993, 290, method A; MS (EI) 233 (M+)) according to the general procedure K. Obtained as an orange solid (367 mg).

Workup

  1. customdescribed in Synthesis, 1993, 290, method A

Sources & evidence

ORD record
ord-2544bdda83574c4db90da7425bad165a
Source dataset
uspto-grants-2005_11
Patent number
US06960578B2

Reaction notes

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