Hydrochloric Acid → (S)-2-[5-Naphthalen-1-yl-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid

HRID 7808Notes

Reaction equation

HRID 7808 reaction equation
C[O:2][C:3](=[O:42])[C@@H:4]([N:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][CH:19]=2)[CH:15]=[C:14]([NH:28][C:29](=[O:40])[C:30]2[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=2)[C:13]1=[O:41])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Li+].Cl>O1CCCC1>[C:18]1([C:16]2[CH:15]=[C:14]([NH:28][C:29](=[O:40])[C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:32][CH:31]=3)[C:13](=[O:41])[N:12]([C@@H:4]([CH2:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]([OH:42])=[O:2])[CH:17]=2)[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 69587926(S)-2-[5-Naphthalen-1-yl-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester

Product 1

HCID 58680180(S)-2-[5-Naphthalen-1-yl-2-oxo-3-(4-trifluoromethylbenzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-[5-naphthalen-1-yl-2-oxo-3-(4-trifluoromethyl-benzoylamino)-2H-pyridin-1-yl]-3-phenylpropionic acid methyl ester from Step F (31 mg, 0.054 mmol) and 1N lithium hydroxide (2.0 mL) in tetrahydrofuran (2.0 mL) was stirred at room temperature for 1 h. 1N Hydrochloric acid (3 mL) was added and the mixture was extracted with dichloromethane (3×10 mL). The combined organic layer was dried with sodium sulfate, filtered and concentrated in vacuo to give a quantitative yield of the title compound. MS 557.1 (M+H)+.

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic layer was dried with sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2bc70584fccd43939cccf6094ec7e59c
Source dataset
uspto-grants-2006_08
Patent number
US07087622B2

Reaction notes

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