Water → HCID 59314405, compound

HRID 1047730Notes

Reaction equation

HRID 1047730 reaction equation
C([O:3][C:4]([C:6]1([NH:16][C:17]([C:19]2[C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=3[CH:22]=[CH:21][CH:20]=2)=[O:18])[CH2:15][C:9]2=[C:10]([CH3:14])[S:11][C:12]([CH3:13])=[C:8]2[CH2:7]1)=[O:5])C.[OH-].[K+].O>CCO>[CH3:14][C:10]1[S:11][C:12]([CH3:13])=[C:8]2[CH2:7][C:6]([NH:16][C:17]([C:19]3[C:28]4[CH2:27][CH2:26][CH2:25][CH2:24][C:23]=4[CH:22]=[CH:21][CH:20]=3)=[O:18])([C:4]([OH:5])=[O:3])[CH2:15][C:9]=12

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593142691,3-Dimethyl-5-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acid ethyl ester

Product 1

HCID 59314405HCID 59314405, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 1,3-dimethyl-5-[(5,6,7,8-tetrahydro-naphthalene-1-carbonyl)-amino]-5,6-dihydro-4H-cyclopenta[c]thiophene-5-carboxylic acid ethyl ester (74) (942 mg, 2.37 mmol) and KOH (3 g, 23 mmol) is dissolved in EtOH (20 mL) and water (1 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until no more precipitate formed. The precipitate is filtered to give a pure product (75) as a pale brown solid (832 mg, 95%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (20 mL)
  6. customformed
  7. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-b168d7b6e83c4cee9b9f2c78d17a6846
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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