Hydrochloric Acid → HCID 68226438, compound

HRID 1952665Notes

Reaction equation

HRID 1952665 reaction equation
C[O:2][C:3](=[O:37])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:26](=[O:36])[NH:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([OH:35])[CH:30]=2)=[CH:20][C:21]=1[C:22]([F:25])([F:24])[F:23])=[O:16])[CH2:5][NH:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8].O.[OH-].[Li+].Cl>C1COCC1.O>[OH:35][C:31]1[CH:30]=[C:29]([CH:34]=[CH:33][CH:32]=1)[CH2:28][NH:27][C:26]([C:19]1[S:18][C:17]([C:15]([NH:14][C@@H:4]([CH2:5][NH:6][C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[C:3]([OH:37])=[O:2])=[O:16])=[C:21]([C:22]([F:25])([F:24])[F:23])[CH:20]=1)=[O:36]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226450HCID 68226450, compound

Product 1

HCID 68226438HCID 68226438, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-{[5-(3-Hydroxy-benzylcarbamoyl)-3-trifluoromethyl-thiophene-2-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (40 mg, 0.072 mmol) in THF (5 mL) was added a solution of lithium hydroxide monohydrate (30 mg, 0.71 mmol) in water (6 mL). The mixture was then stirred at room temperature 4 h. The mixture was then acidified with 1N HCl and extracted with EtOAc (×3). The extracts were combined, washed with water and brine, dried over sodium sulfate, filtered, and evaporated to pure product, 26.7 mg (68%). MS m/e 542.0 (M+H+).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to pure product, 26.7 mg (68%)

Sources & evidence

ORD record
ord-7b6b91fc383b400fb3ca9ab5f1db8957
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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