Hydrochloric Acid → HCID 60202702, compound

HRID 1952675Notes

Reaction equation

HRID 1952675 reaction equation
C[O:2][C:3](=[O:35])[C@@H:4]([NH:14][C:15]([C:17]1[S:18][C:19]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=2)=[CH:20][C:21]=1[C:22]#[N: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>[C:22]([C:21]1[CH:20]=[C:19]([C:24](=[O:34])[NH:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([OH:33])[CH:28]=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:35])=[O:2])=[O:16])#[N:23]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 68226525HCID 68226525, compound

Product 1

HCID 60202702HCID 60202702, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-2-{[3-Cyano-5-(3-hydroxy-benzylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-[(thiophene-2-carbonyl)-amino]-propionic acid methyl ester (16.2 mg, 0.032 mmol) in THF (1 mL) was added a solution of lithium hydroxide monohydrate (9 mg, 0.009 mmol) in water (1 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. Material was purified by reverse phase HPLC to afford to pure product, 1.7 mg (11%). MS m/e 498.9 (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
  6. customMaterial was purified by reverse phase HPLC
  7. customto afford to pure product, 1.7 mg (11%)

Sources & evidence

ORD record
ord-2f3c5168fe8b4d7ca64a9a70236099b8
Source dataset
uspto-grants-2013_03
Patent number
US08404859B2

Reaction notes

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