Methanol → HCID 178522248, compound

HRID 1675335Notes

Reaction equation

HRID 1675335 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])=[C:32]([F:38])[CH:31]=4)=[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:31]=[C:32]([F:38])[C:33]([F:37])=[C:34]([F:36])[CH:35]=2)=[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 59179735HCID 59179735, compound2×

Product 1

HCID 178522248HCID 178522248, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of lithium hydroxide (1.61 g, 38.3 mmol) in water (10 mL) was added in one portion to a solution of 4-(3-fluoro-4-{[5-(3,4,5-trifluoro-phenylamino)-[1,3,4]oxadiazole-2-carbonyl]-amino}-phenoxy)-cyclohexanecarboxylic acid ethyl ester (Intermediate 2, 2.0 g, 3.83 mmol) in a 1:1 mixture of THF and methanol (60 mL) was added and the mixture 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 (1.1 g, 58%).

Workup

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

Sources & evidence

ORD record
ord-0b8034a963924582a7440f550a532d80
Source dataset
uspto-grants-2011_08
Patent number
US08003676B2

Reaction notes

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