Trifluoroacetic acid → 4-[1-{5-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-pyrrol-2-yl}-2-(tetrahydro-2H-pyran-4-yl)ethyl]benzoic acid

HRID 1881995Notes

Reaction equation

HRID 1881995 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[NH:12][C:11]([CH:13]([C:21]3[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][CH:22]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)=[N:5][CH:4]=1.FC(F)(F)C(O)=O>ClCCl>[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[NH:12][C:11]([CH:13]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:32][CH:33]=3)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:10][CH:9]=2)=[N:5][CH:4]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59331271HCID 59331271, compound

Product 1

HCID 593312214-[1-{5-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-pyrrol-2-yl}-2-(tetrahydro-2H-pyran-4-yl)ethyl]benzoic acidYield 34.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[1-{5-[5-(hydroxymethyl)-1,3-thiazol-2-yl]-1H-pyrrol-2-yl}-2-(tetrahydro-2H-pyran-4-yl)ethyl]benzoate (200 mg) in dichloromethane (10 mL) was added trifluoroacetic acid (2 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated and subjected to preparative HPLC to give the title compound (60.0 mg, yield 34%) as a pale-yellow solid. MS: 413 (MH+).

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-9767e83f003247d2b7bc7631a30735cb
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…