Hydrochloric Acid → HCID 60202701, compound

HRID 1952670Notes

Reaction equation

HRID 1952670 reaction equation
C[O:2][C:3](=[O:38])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:25](=[O:37])[NH:26][CH2:27][C:28]2[CH:36]=[CH:35][CH:34]=[C:33]3[C:29]=2[CH:30]=[N:31][NH:32]3)=[CH:20][C:21]=1[CH:22]([CH3:24])[CH3:23])=[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>[NH:32]1[C:33]2[C:29](=[C:28]([CH2:27][NH:26][C:25]([C:19]3[S:18][C:17]([C:15]([NH:14][C@@H:4]([CH2:5][NH:6][C:7]([C:9]4[S:10][CH:11]=[CH:12][CH:13]=4)=[O:8])[C:3]([OH:38])=[O:2])=[O:16])=[C:21]([CH:22]([CH3:24])[CH3:23])[CH:20]=3)=[O:37])[CH:36]=[CH:35][CH:34]=2)[CH:30]=[N:31]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226623HCID 68226623, compound

Product 1

HCID 60202701HCID 60202701, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-({5-[(1H-Indazol-4-ylmethyl)-carbamoyl]-3-isopropyl-thiophene-2-carbonyl}-amino)-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (109.6 mg, 0.020 mmol) in THF (4 mL) was added a solution of lithium hydroxide monohydrate (84 mg, 2.0 mmol) in water (6 mL). The mixture was then stirred at room temperature 2 d. 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, 85.8 mg (79%). MS m/e 540.0 (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, 85.8 mg (79%)

Sources & evidence

ORD record
ord-dc19daf342ad4088af0a359931397c63
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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