Trifluoroacetic acid → 4-Butoxy-benzenesulfonic acid 4-(3-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-ylamino]-2-hydroxy-propoxy}-phenyl Ester

HRID 479960Notes

Reaction equation

HRID 479960 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:18][CH:17]([N:19](C(OC(C)(C)C)=O)[CH2:20][CH:21]([OH:45])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][S:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:35]=4)(=[O:33])=[O:32])=[CH:26][CH:25]=3)[CH2:16]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[CH2:16][CH:17]([NH:19][CH2:20][CH:21]([OH:45])[CH2:22][O:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][S:31]([C:34]4[CH:39]=[CH:38][C:37]([O:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:35]=4)(=[O:32])=[O:33])=[CH:26][CH:25]=3)[CH2:18]2)(=[O:14])=[O:13])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 121144784-Butoxy-benzenesulfonic acid 4-(3-{[1-(4-butoxybenzene-sulfonyl)azetidin-3-yl]-tert-butoxycarbonyl-amino}-2-hydroxy-propoxy)-phenylester

Product 1

HCID 121144794-Butoxy-benzenesulfonic acid 4-(3-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-ylamino]-2-hydroxy-propoxy}-phenyl EsterYield 100.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-butoxy-benzenesulfonic acid 4-(3-{[1-(4-butoxybenzene-sulfonyl)azetidin-3-yl]-tert-butoxycarbonyl-amino}-2-hydroxy-propoxy)-phenylester (0.12 g, 0.15 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid (0.12 ml, 1.5 mmol). The mixture was stirred at room temperature for 4 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; MS (ES) m/z 663.1 (MH+); HRMS (ES) Calcd. for C32H43N2O9S2 (MH+): 663.2410, Found: 663.2401.

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-15fd1643d866420eb1713479a73b407a
Source dataset
uspto-grants-2003_11
Patent number
US06649603B2

Reaction notes

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