Lithium Hydroxide → Trifluoroacetic acid

HRID 2375798Notes

Reaction equation

HRID 2375798 reaction equation
C[O:2][C:3]([C:5]1[N:6]([CH2:22][C:23]2[CH:27]=[C:26]([C:28]3[S:29][C:30]([Cl:33])=[CH:31][CH:32]=3)[O:25][N:24]=2)[C:7]([C:10](=[O:21])[NH:11][CH:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)=[CH:8][CH:9]=1)=[O:4].[Li+].[OH-].[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]>C1COCC1.O>[Cl:33][C:30]1[S:29][C:28]([C:26]2[O:25][N:24]=[C:23]([CH2:22][N:6]3[C:7]([C:10](=[O:21])[NH:11][CH:12]4[CH2:13][CH2:14][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:16][CH2:17]4)=[CH:8][CH:9]=[C:5]3[C:3]([OH:4])=[O:2])[CH:27]=2)=[CH:32][CH:31]=1.[C:36]([OH:42])([C:38]([F:41])([F:40])[F:39])=[O:37]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 6422Trifluoroacetic acidHCID 69289972HCID 69289972, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.05%HCID 23085251HCID 23085251, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
45 °C

Procedure

To a solution of 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid methyl ester (example 10, 30 mg) in 5 mL of THF/water(3:1) was added LiOH (9 mg) The mixture was stirred for 2 h at 45° C. after which it was cooled to RT, acidified with TFA and concentrated. 1-[5-(5-Chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-5-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-pyrrole-2-carboxylic acid was obtained after preparative HPLC(CH3CN/H2O gradient+0.05% TFA) of the residue. MS (ESI+): m/e=477 [M+H]+, chloro pattern.

Workup

  1. temperaturewas cooled to RT
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-b9d536edc4c3497ba1396b13e4c16305
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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