Hydrochloric Acid → HCID 178461279, compound

HRID 1190013Notes

Reaction equation

HRID 1190013 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[S:15][C:14]([C:16]([OH:18])=[O:17])=[C:13]([N:19]([C@H:29]4[CH2:34][CH2:33][C@H:32]([OH:35])[CH2:31][CH2:30]4)[C:20]([C@H:22]4[CH2:27][CH2:26][C@H:25]([CH3:28])[CH2:24][CH2:23]4)=[O:21])[CH:12]=3)=[CH:7][CH2:6]2)[O:4]CC1.Cl>C1COCC1.C(Cl)Cl>[OH:35][C@H:32]1[CH2:33][CH2:34][C@H:29]([N:19]([C:20]([C@H:22]2[CH2:23][CH2:24][C@H:25]([CH3:28])[CH2:26][CH2:27]2)=[O:21])[C:13]2[CH:12]=[C:11]([C:8]3[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH:7]=3)[S:15][C:14]=2[C:16]([OH:18])=[O:17])[CH2:30][CH2:31]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178461267HCID 178461267, compound

Product 1

HCID 178461279HCID 178461279, compoundYield 71.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (428 mg, 0.85 mmol) in THF (5 mL) was added 3N HCl (2.5 mL), and the mixture was heated at 40° C. for 5 h. Then it was diluted with CH2Cl2 (70 mL) and washed with brine and water. Organic fraction was dried over Na2SO4, concentrated under reduced pressure and the residue was purified by column chromatography on silica gel eluting with 0-10% MeOH in CH2Cl2 to give 278 mg (71%) of 3-[(trans-4-hydroxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4-oxo-cyclohex-1-enyl)-thiophene-2-carboxylic acid.

Workup

  1. washwashed with brine and water
  2. dry with materialOrganic fraction was dried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by column chromatography on silica gel eluting with 0-10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-e74621ce079048f1b4c34f390aca7c3c
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

Loading…