Chloroform → HCID 68114598, compound

HRID 1200141Notes

Reaction equation

HRID 1200141 reaction equation
C1(S)C=CC=CC=1.C(Cl)(Cl)Cl.[CH3:12][C:13]([NH:21][C:22](=[O:43])[C@@H:23]([NH:35]C(OC(C)(C)C)=O)[CH2:24][S:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)([CH3:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47]>C(OCC)C.CCCCCC>[F:44][C:45]([F:50])([F:49])[C:46]([OH:48])=[O:47].[CH3:20][C:13]([NH:21][C:22](=[O:43])[C@@H:23]([NH2:35])[CH2:24][S:25][CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)([CH3:12])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 6212ChloroformHCID 6422Trifluoroacetic acidHCID 7969ThiophenolHCID 53917307HCID 53917307, compound

Product 1

HCID 68114598HCID 68114598, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

1.6 g of thiophenol was added to 20 ml of a chloroform solution containing 6.093 g of (2R)-N-(α,α-dimethylbenzyl)-2-(t-butoxycarbonylamino)-3-(p-methoxybenzylthio)propionamide (prepared as described in Preparation 6), and then the mixture was placed over an ice-water bath, and 15 ml of trifluoroacetic acid were added; the mixture was stirred for 20 minutes at the temperature of the ice-water bath. After additional stirring for 1.5 hours at room temperature, the solvent and excess reagents were distilled off under reduced pressure. The residue obtained was dissolved in 7 ml of diethyl ether and addition of 50 ml hexane afforded the title compound.

Workup

  1. customthe mixture was placed over an ice-water bath
  2. distillationthe solvent and excess reagents were distilled off under reduced pressure
  3. customThe residue obtained

Sources & evidence

ORD record
ord-b37040aaa1894d099e237e959e8e3b49
Source dataset
uspto-grants-1990_02
Patent number
US04904680

Reaction notes

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