Dichloromethane → HCID 131732534, compound

HRID 870378Notes

Reaction equation

HRID 870378 reaction equation
C(OC(=O)[N:7]([C@H:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([NH:21][S:22]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH:32]([F:34])[F:33])=[CH:27][CH:26]=3)(=[O:24])=[O:23])[CH:17]=2)[CH2:12]1)[CH2:8][CH2:9][CH3:10])(C)(C)C.FC(F)(F)C(O)=O.[Cl:43]CCl>>[ClH:43].[F:34][CH:32]([F:33])[O:31][C:28]1[CH:29]=[CH:30][C:25]([S:22]([NH:21][C:16]2[CH:15]=[CH:14][C:13]3[CH2:12][C@@H:11]([NH:7][CH2:8][CH2:9][CH3:10])[CH2:20][CH2:19][C:18]=3[CH:17]=2)(=[O:24])=[O:23])=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68916746HCID 68916746, compound

Product 1

HCID 131732534HCID 131732534, compoundYield 77%

Procedure

[(S)-6-(4-Difluoromethoxy-benzenesulfonylamino)-1,2,3,4-tetrahydro-naphthalen-2-yl]-propyl-carbamic acid tert-butyl ester (2.08 g, 4.07 mmol) were dissolved in dichloromethane (100 ml). Trifluoroacetic acid (10 ml) was added and the reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was evaporated to dryness. Diethyl ether (100 ml) was added and the mixture was extracted with saturated NaHCO3 solution. To the organic layer was added ethereal hydrochloride solution and the solvent evaporated. To the residue was added diethyl ether (25 ml) and the resulting crystalline product was filtered off to give pure product (1.41 g, 77% yield).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionDiethyl ether (100 ml) was added
  3. extractionthe mixture was extracted with saturated NaHCO3 solution
  4. additionTo the organic layer was added ethereal hydrochloride solution
  5. customthe solvent evaporated
  6. additionTo the residue was added diethyl ether (25 ml)
  7. filtrationthe resulting crystalline product was filtered off

Sources & evidence

ORD record
ord-9b541fdce17c4fd38856bded1849d50a
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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