Water → HCID 23075279, compound

HRID 2076435Notes

Reaction equation

HRID 2076435 reaction equation
[F:1][C:2]([F:30])([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([CH3:27])([CH3:26])[CH2:21][CH2:20][C:19]2([CH3:29])[CH3:28])[C:3]([NH:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1)=[O:4].O.[OH-].[Na+]>CO>[F:1][C:2]([F:30])([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([CH3:26])([CH3:27])[CH2:21][CH2:20][C:19]2([CH3:29])[CH3:28])[C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1)=[O:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 23075285HCID 23075285, compound

Product 1

HCID 23075279HCID 23075279, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

4-[2,2-Difluoro-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-acetylamino]-benzoic acid methyl ester 17 (500 mg, 1.20 mmol) was dissolved in methanol (33.5 mL). Water (3.35 mL) and NaOH (270 mg, 4.81 mmol) were successively added at RT. The mixture was stirred at 70° C. for 1 h. The mixture was evaporated in vacuo and dissolved in water (100 ml) and extracted with diethyl ether (2×50 mL). The aqueous layer was acidified by HCl (1M) to about pH=1 and extracted with diethyl ether (2×100 mL), the organic layer was dried over MgSO4, filtered and evaporated. 4-(2,2-Difluoro-2-(1,2,3,4-tetrahydro-1,1,4,4-tetramethylnaphthalen-6-yl)acetamido)benzoic acid 18 was obtained (169 mg, 35% yield) as a beige solid.

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutiondissolved in water (100 ml)
  3. extractionextracted with diethyl ether (2×50 mL)
  4. extractionextracted with diethyl ether (2×100 mL)
  5. dry with materialthe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-7167e44946de4cd2ba043e4c2eca84d4
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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