Methanol → HCID 178522247, compound

HRID 1675332Notes

Reaction equation

HRID 1675332 reaction equation
[OH-].[Li+].C([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][C:22]([C:24]3[O:25][C:26]([NH:29][C:30]4[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=4[F:38])=[N:27][N:28]=3)=[O:23])=[C:17]([F:39])[CH:16]=2)[CH2:10][CH2:9]1)=[O:7])C.C1COCC1.CO>O>[F:39][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[NH:21][C:22]([C:24]1[O:25][C:26]([NH:29][C:30]2[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=2[F:38])=[N:27][N:28]=1)=[O:23])[O:14][C@@H:11]1[CH2:10][CH2:9][C@H:8]([C:6]([OH:7])=[O:5])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 59179741HCID 59179741, compound2×

Product 1

HCID 178522247HCID 178522247, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of lithium hydroxide (965 mg, 23.0 mmol) in water (5 mL) was added in one portion to a solution of 4-(3-fluoro-4-{[5-(2,4,5-trifluoro-phenylamino)-[1,3,4]oxadiazole-2-carbonyl]-amino}-phenoxy)-cyclohexanecarboxylic acid ethyl ester (Intermediate 1, 1.2 g, 2.3 mmol) in a 1:1 mixture of THF and methanol (50 mL) and the mixture was stirred at ambient temperature for 4 h. The mixture was concentrated in vacuo, acidified with a 1M aqueous solution of citric acid and then filtered to leave a solid. The solid was washed with water, dried and recrystallised from ethanol (30 mL) to give the title compound as a white solid (700 mg, 64%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. filtrationfiltered
  3. customto leave a solid
  4. washThe solid was washed with water
  5. customdried
  6. customrecrystallised from ethanol (30 mL)

Sources & evidence

ORD record
ord-fed88a6b5981451399f2bbfb53a067fb
Source dataset
uspto-grants-2011_08
Patent number
US08003676B2

Reaction notes

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