Dichloromethane → HCID 131732535, compound

HRID 870380Notes

Reaction equation

HRID 870380 reaction equation
C(OC(=O)[N:7]([CH2:33][CH2:34][CH3:35])[C@H:8]1[CH2:17][CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([NH:18][S:19]([C:22]3[CH:27]=[CH:26][C:25]([CH2:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:14]=2)[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O.[Cl:44]CCl>>[ClH:44].[CH2:33]([NH:7][C@H:8]1[CH2:17][CH2:16][C:15]2[CH:14]=[C:13]([NH:18][S:19]([C:22]3[CH:23]=[CH:24][C:25]([CH2:28][C:29]([F:32])([F:30])[F:31])=[CH:26][CH:27]=3)(=[O:21])=[O:20])[CH:12]=[CH:11][C:10]=2[CH2:9]1)[CH2:34][CH3:35]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 68914455HCID 68914455, compound

Product 1

HCID 131732535HCID 131732535, compoundYield 65%

Procedure

Propyl-{(S)-6-[4-(2,2,2-trifluoro-ethyl)-benzenesulfonylamino]-1,2,3,4-tetrahydronaphthalen-2-yl}-carbamic acid tert-butyl ester (1.22 g, 2.07 mmol) was dissolved in dichloromethane (40 ml). Trifluoroacetic acid (2 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. The organic layer was dried over magnesium sulfate, filtered, and the solvent evaporated under reduced pressure. The residue was dissolved with ethyl acetate and ethereal hydrochloride solution was added. The crystalline product was filtered off to give pure product (625 mg, 65% 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. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated under reduced pressure
  7. dissolutionThe residue was dissolved with ethyl acetate and ethereal hydrochloride solution
  8. additionwas added
  9. filtrationThe crystalline product was filtered off

Sources & evidence

ORD record
ord-acfc7ee5bea04add9a1a0391bc7715b8
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

Loading…