Trifluoroacetic acid → 4-{(2S)-3-[1-(4-Butoxy-benzenesulfonyl)-azetidin-3-ylamino]-2-hydroxy-propoxy}-phenol

HRID 2300231Notes

Reaction equation

HRID 2300231 reaction equation
C(OC(=O)[N:7]([CH:20]1[CH2:23][N:22]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][CH3:37])=[CH:29][CH:28]=2)(=[O:26])=[O:25])[CH2:21]1)[CH2:8][C@H:9]([OH:19])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:34]([O:33][C:30]1[CH:29]=[CH:28][C:27]([S:24]([N:22]2[CH2:21][CH:20]([NH:7][CH2:8][C@H:9]([OH:19])[CH2:10][O:11][C:12]3[CH:13]=[CH:14][C:15]([OH:18])=[CH:16][CH:17]=3)[CH2:23]2)(=[O:25])=[O:26])=[CH:32][CH:31]=1)[CH2:35][CH2:36][CH3:37]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 12114477[1-(4-Butoxy-benzenesulfonyl)-azetidin-3-yl]-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamic acid tert-butyl ester

Product 1

HCID 98250074-{(2S)-3-[1-(4-Butoxy-benzenesulfonyl)-azetidin-3-ylamino]-2-hydroxy-propoxy}-phenolYield 111%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-[(2S)-2-hydroxy-3-(4-hydroxy-phenoxy)-propyl]-carbamic acid tert-butyl ester (0.11 g, 0.2 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (0.15 ml, 2 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 to give 0.10 g of a white solid; m.p. 55-58° C.; MS (ES) m/z 451 (MH+); HRMS (Cl) Calcd. for C22H31N2O6S (MH+): 451.1903, Found: 451.1882.

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

Sources & evidence

ORD record
ord-9c4d763ae32d47018cac2cb7228ed125
Source dataset
uspto-grants-2002_12
Patent number
US06498170B2

Reaction notes

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