3-(3-Benzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert-butyl ester → 3-(3-Benzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid

HRID 1872263Notes

Reaction equation

HRID 1872263 reaction equation
C([O:5][C:6]([CH:8]1[CH:14]([NH:15][C:16]([NH:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH2:13][CH:12]=[CH:11][CH2:10][N:9]1[S:26]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)(=[O:28])=[O:27])=[O:7])(C)(C)C.C(OC(C1(C(=O)N)C(CCC2C=CC=CC=2)CCCCN1S(C1C=CC(OC)=CC=1)(=O)=O)=O)(C)(C)C>>[CH2:19]([NH:18][C:16](=[O:17])[NH:15][CH:14]1[CH2:13][CH:12]=[CH:11][CH2:10][N:9]([S:26]([C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)(=[O:28])=[O:27])[CH:8]1[C:6]([OH:7])=[O:5])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 120878733-(3-Benzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert-butyl esterHCID 700746191-(4-Methoxybenzenesulfonyl)-3-phenethyl carbamoyl-azepane-2-carboxylic acid tert-butyl ester

Product 1

HCID 120878743-(3-Benzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid

Procedure

3-(3-Benzylureido)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid tert-butyl ester (25 mg, 0.05 mmol) is reacted in the same manner as 1-(4-Methoxybenzenesulfonyl)-3-phenethyl carbamoyl-azepane-2-carboxylic acid tert-butyl ester and purified by flash-chromatography, Dichloromethane/Methanol (9:1): Cal. 458.5 found (M-H)+ 458.2; 1H NMR (DMSO, 400 MHz), ppm: 7.79 (d, 2H), 7.30 (m, 2H),7.20 (m, 3H) 7.02 (d, 2H), 5.60 (m, 1H), 5.50 (m, 1H) 4.3 (m, 3H), 4.00 (m, 1H), 3.93 (m, 3H), 2.81 (t, 2H),2.35 (m, 2H), 2.05 (m, 2H).

Workup

  1. custompurified by flash-chromatography, Dichloromethane/Methanol (9:1)

Sources & evidence

ORD record
ord-3d514afe73444a04a14f244b54002bdd
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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