Hydrochloric Acid → HCID 68226478, compound

HRID 1952673Notes

Reaction equation

HRID 1952673 reaction equation
C[O:2][C:3](=[O:34])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:23](=[O:33])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)=[CH:20][C:21]=1[Br: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>[Br:22][C:21]1[CH:20]=[C:19]([C:23](=[O:33])[NH:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([OH:32])[CH:27]=2)[S:18][C:17]=1[C:15]([NH:14][C@@H:4]([CH2:5][NH:6][C:7]([C:9]1[S:10][CH:11]=[CH:12][CH:13]=1)=[O:8])[C:3]([OH:34])=[O:2])=[O:16]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226589HCID 68226589, compound

Product 1

HCID 68226478HCID 68226478, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-{[3-Bromo-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (24.2 mg, 0.043 mmol) in THF (3 mL) was added a solution of lithium hydroxide monohydrate (120 mg, 2.87 mmol) in water (4 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, 20.6 mg (87%). MS m/e 553.8 (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, 20.6 mg (87%)

Sources & evidence

ORD record
ord-99be1fa90a1a4d29ad1d613a61dc4896
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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