Trifluoroacetic acid → HCID 10122037, compound

HRID 351714Notes

Reaction equation

HRID 351714 reaction equation
C([O:5][C:6](=[O:47])[C:7]([CH2:43][C:44]#[C:45][CH3:46])([S:12]([C:15]1[CH:20]=[CH:19][C:18]([N:21]2[CH2:26][CH2:25][CH:24]([NH:27][CH2:28][C@H:29]([OH:42])[C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][S:38]([CH3:41])(=[O:40])=[O:39])[CH:31]=3)[CH2:23][CH2:22]2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:8][C:9]#[C:10][CH3:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:8]([C:7]([S:12]([C:15]1[CH:16]=[CH:17][C:18]([N:21]2[CH2:26][CH2:25][CH:24]([NH:27][CH2:28][C@H:29]([OH:42])[C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[C:32]([NH:37][S:38]([CH3:41])(=[O:39])=[O:40])[CH:31]=3)[CH2:23][CH2:22]2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])([CH2:43][C:44]#[C:45][CH3:46])[C:6]([OH:47])=[O:5])[C:9]#[C:10][CH3:11]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10305415HCID 10305415, compound

Product 1

HCID 10122037HCID 10122037, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-butynyl)-2-[(4-{4-[((2R)-2-hydroxy-2-(4-hydroxy-3-[(methylsulfonyl)amino]-phenyl}ethyl)amino]-1-piperidinyl)phenyl)sulfonyl]-4-hexynoicacid tert-butyl ester 0.21 g (0.3 mmol) in dichloromethane (3 ml) was added trifluoroacetic acid (0.23 ml, 3 mmol), and the mixture was stirred at room temperature for 2 days. It was then evaporated and treated with 10% sodium bicarbonate solution until pH 6. The resulting suspension was filtered and the precipitate washed with water, and dried in vacuo to give 85 mg of a beige solid; m.p. 175-177° C.; MS (ES) m/z 630.6 (M−H—); HRMS (EI) Calcd. for C30H36N3O8S2 (M−H−): 630.1949, Found: 630.1943.

Workup

  1. customIt was then evaporated
  2. additiontreated with 10% sodium bicarbonate solution until pH 6
  3. filtrationThe resulting suspension was filtered
  4. washthe precipitate washed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-56e2e08c127d42c989440d2f8c767706
Source dataset
uspto-grants-2004_06
Patent number
US06743787B2

Reaction notes

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