Trifluoroacetic acid → HCID 18767796, compound

HRID 479947Notes

Reaction equation

HRID 479947 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 (EI) 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-7d2fb396a48d412ca261db153ffe1033
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

Loading…