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Hydrochloric Acid → HCID 67672163, compound

HRID 1417551
Notes
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Reaction equation

HRID 1417551 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:30][CH2:29][C@:7]2([O:11][CH2:10][C@H:9]([C:12]3[CH:17]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[C:19]4[C:23]([F:26])([F:25])[F:24])[CH:15]=[CH:14][C:13]=3[O:27][CH3:28])[CH2:8]2)[C@@H:6]1[C:31]1[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=1)=[O:4].[OH-].[Na+].Cl>C(O)C.O>[F:37][C:34]1[CH:35]=[CH:36][C:31]([C@H:6]2[C@@H:5]([C:3]([OH:4])=[O:2])[CH2:30][CH2:29][C@@:7]32[O:11][CH2:10][C@H:9]([C:12]2[CH:17]=[C:16]([N:18]4[CH:22]=[CH:21][N:20]=[C:19]4[C:23]([F:26])([F:25])[F:24])[CH:15]=[CH:14][C:13]=2[O:27][CH3:28])[CH2:8]3)=[CH:32][CH:33]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 56974282HCID 56974282, compound

Product 1

HCID 67672163HCID 67672163, compoundYield 103%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent
HCID 962
Water
Solvent

Conditions

Temperature
0 °C

Procedure

To an ice cold solution of 40 mg (0.077 mmol) (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-trifluoromethylimidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester (from Example 70) in 1.0 mL of ethanol and 0.20 mL of water was added 0.050 mL of 2.5N aqueous NaOH. The mixture was stirred at 0° C., then warmed slowly to RT overnight. After neutralizing with 0.065 mL of 2N aqueous HCl, the mixture was partitioned between 25 mL of ethyl acetate and 25 mL of brine. The layers were separated and the organic layer was dried over sodium sulfate and evaporated to give 40 mg of title compound as a colorless syrup. Mass spectrum (NH3/CI): m/z=505.0 (M+1).

Workup

  1. temperaturewarmed slowly to RT overnight
  2. customthe mixture was partitioned between 25 mL of ethyl acetate and 25 mL of brine
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-734052d1bf674d6f8fb9fffa361c78b1
Source dataset
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05877191

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes