Hydrochloric Acid → HCID 68226958, compound

HRID 1952674Notes

Reaction equation

HRID 1952674 reaction equation
C[O:2][C:3](=[O:35])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:34])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[C:28]([OH:33])[CH:27]=2)=[CH:20][C:21]=1[CH3:22])=[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>[F:32][C:29]1[CH:30]=[CH:31][C:26]([CH2:25][NH:24][C:23]([C:19]2[S:18][C:17]([C:15]([NH:14][C@@H:4]([CH2:5][NH:6][C:7]([C:9]3[S:10][CH:11]=[CH:12][CH:13]=3)=[O:8])[C:3]([OH:35])=[O:2])=[O:16])=[C:21]([CH3:22])[CH:20]=2)=[O:34])=[CH:27][C:28]=1[OH:33]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226698HCID 68226698, compound

Product 1

HCID 68226958HCID 68226958, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-{[5-(4-Fluoro-3-hydroxy-benzylcarbamoyl)-3-methyl-thiophene-2-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acidmethyl ester (14 mg, 0.027 mmol) in THF (2 mL) was added a solution of lithium hydroxide monohydrate (11 mg, 0.269 mmol) in water (2.5 mL). The mixture was then stirred at room temperature 15 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, 12.3 mg (68%). MS m/e 506.2 (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, 12.3 mg (68%)

Sources & evidence

ORD record
ord-6a90d685ab994ba3b0ee4f057d3ce489
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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