Trifluoroacetic acid → HCID 18767796, compound

HRID 2300218Notes

Reaction equation

HRID 2300218 reaction equation
C(OC(=O)[N:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH:8]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:26]([NH:7][CH:8]1[CH2:11][N:10]([S:12]([C:15]2[CH:16]=[CH:17][C:18]([NH:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH2:9]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18767793HCID 18767793, compound

Product 1

HCID 18767796HCID 18767796, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Benzyl-[1-(4-butylamino-benzenesulfonyl)-azetidin-3-yl]-carbamicacid tert-butyl ester (0.19 g, 0.4 mmol) in dichloromethane (4 ml) was added trifluoroacetic acid (0.31 ml, 4 mmol). The mixture was stirred at room temperature for 2 h, and then quenched with saturated sodium carbonate solution, and extracted with dichloromethane. The organic solution was washed with brine, dried over sodium sufate, and evaporated. The crude product was chromatographed on silica gel (ethyl acetate-hexanes/3:2) to give 0.09 g of a colorless foam; MS (ES) m/z 374.1 (MH+); HRMS (El) Calcd. for C20H27N3O2S (M+): 373.1824, Found: 373.1822.

Workup

  1. customquenched with saturated sodium carbonate solution
  2. extractionextracted with dichloromethane
  3. washThe organic solution was washed with brine
  4. dry with materialdried over sodium sufate
  5. customevaporated
  6. customThe crude product was chromatographed on silica gel (ethyl acetate-hexanes/3:2)

Sources & evidence

ORD record
ord-0f75872656e54af789d998cc1323db6c
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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