Hydrochloric Acid → HCID 68226643, compound

HRID 1952664Notes

Reaction equation

HRID 1952664 reaction equation
C[O:2][C:3](=[O:40])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:26](=[O:39])[NH:27][CH2:28][C:29]2[CH:37]=[CH:36][CH:35]=[C:34]3[C:30]=2[CH2:31][C:32](=[O:38])[NH:33]3)=[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>[O:38]=[C:32]1[CH2:31][C:30]2[C:34](=[CH:35][CH:36]=[CH:37][C:29]=2[CH2:28][NH:27][C:26]([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:40])=[O:2])=[O:16])=[C:21]([C:22]([F:25])([F:24])[F:23])[CH:20]=2)=[O:39])[NH:33]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226763HCID 68226763, compound

Product 1

HCID 68226643HCID 68226643, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-({5-[(2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-carbamoyl]-3-trifluoromethyl-thiophene-2-carbonyl}-amino)-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (53 mg, 0.089 mmol) in THF (5 mL) was added a solution of lithium hydroxide monohydrate (37 mg, 0.89 mmol) in water (6 mL). The mixture was then stirred at room temperature 5 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, 0.0466 g (90%). MS m/e 581.0 (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, 0.0466 g (90%)

Sources & evidence

ORD record
ord-caf24a5ec46b47e7aff8b1b4890bc838
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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