Hydrochloric Acid → HCID 178499251, compound

HRID 1694434Notes

Reaction equation

HRID 1694434 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:30])=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:29][CH2:28][C:23]2(OCC[O:24]2)[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>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:30])=[CH:8][C:9]=1[N:10]([C:11]([C@H:13]1[CH2:14][CH2:15][C@H:16]([CH3:19])[CH2:17][CH2:18]1)=[O:12])[CH:20]1[CH2:29][CH2:28][C:23](=[O:24])[CH2:22][CH2:21]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178499250HCID 178499250, compound

Product 1

HCID 178499251HCID 178499251, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

The 5-bromo-3-[(1,4-dioxa-spiro[4.5]dec-8-yl)-(trans-4-methylcyclohexane-carbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (8.6 g, 17 mmol) was dissolved in tetrahydrofuran (100 ml) and treated with 3N HCl solution (50 ml). The reaction was stirred at 40° C. for 3 hours. The reaction mixture was evaporated under reduced pressure. The residue was dissolved in EtOAc and wash with aq. sat. NaHCO3 solution. The organic layer was separated, dried on Na2SO4, filtered and concentrated to give 5-Bromo-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester as a solid (7.4 g, 95%).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwash with aq. sat. NaHCO3 solution
  4. customThe organic layer was separated
  5. customdried on Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-25b75855a8a14072bdf75be4a1ac30a3
Source dataset
uspto-grants-2012_04
Patent number
US08158675B2

Reaction notes

Loading…