Hydrochloric Acid → HCID 178499305, compound

HRID 1694470Notes

Reaction equation

HRID 1694470 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:28]2[CH2:37][CH2:36][C:31]3(OCC[O:32]3)[CH2:30][CH2:29]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([O:26][CH3:27])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].Cl>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH:28]2[CH2:29][CH2:30][C:31](=[O:32])[CH2:36][CH2:37]2)=[CH:8][C:9]=1[N:10]([C@H:20]1[CH2:25][CH2:24][C@H:23]([O:26][CH3:27])[CH2:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178499260HCID 178499260, compound

Product 1

HCID 178499305HCID 178499305, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The product of step III was dissolved in THF (40 mL), 3N HCl (20 mL) was added to this solution, and the mixture was heated for 3 h at 50° C., then for an additional 3 h at 60° C. The mixture was brought to room temperature, extracted with CH2Cl2, washed with sodium bicarbonate and brine, organic fraction was separated, dried over Na2SO4, and concentrated under reduced pressure. Purification by column chromatography on silica gel using hexanes-EtOAc gradient to afford 726 mg (85%) of 3-[(trans-4-methoxy-cyclohexyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-5-(4-oxocyclohexyl)-thiophene-2-carboxylic acid methyl ester.

Workup

  1. customwas brought to room temperature
  2. extractionextracted with CH2Cl2
  3. washwashed with sodium bicarbonate and brine, organic fraction
  4. customwas separated
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-31f23b32358549d897acbf6591fe26da
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

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