HCID 131727861, compound → HCID 131727860, compound

HRID 1994435Notes

Reaction equation

HRID 1994435 reaction equation
[CH2:1]([O:8][C:9](=[O:52])[NH:10][C:11]([C:26](=[O:51])[NH:27][CH:28]([C:37](=[O:50])[N:38]([CH2:42][CH:43](OCC)OCC)[CH:39]([CH3:41])[CH3:40])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)([CH3:25])[CH2:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])(=[O:16])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)=O>[CH2:1]([O:8][C:9](=[O:52])[NH:10][C:11]1([CH3:25])[C:26](=[O:51])[N:27]2[CH:28]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[C:37](=[O:50])[N:38]([CH:39]([CH3:40])[CH3:41])[CH2:42][CH:43]2[N:13]([S:14]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])(=[O:16])=[O:15])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 131727861HCID 131727861, compound

Product 1

HCID 131727860HCID 131727860, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A solution of 80 mg (0.1 mmol) of benzyl[1-{2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethylcarbamoyl}-2-(2,4-dichlorobenzenesulfonylamino)-1-methylethyl]carbamate in 1.5 ml of HCOOH (99%) is stirred at 60° C. for 24 h. The reaction solution is concentrated in vacuo, and the crude product is purified by chromatography (4 g of SiO2, eluent EtOAc/heptane (gradient 0-50%)). 30 mg of the desired product are obtained as a white solid. MW (calculated, monoisotopic)=706, measured value: (M+H)+=707

Workup

  1. concentrationThe reaction solution is concentrated in vacuo
  2. customthe crude product is purified by chromatography (4 g of SiO2, eluent EtOAc/heptane (gradient 0-50%))

Sources & evidence

ORD record
ord-ffdd32a921f84fbc9da53a5aadf368f0
Source dataset
uspto-grants-2010_01
Patent number
US07652007B2

Reaction notes

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