Hydrochloric Acid → HCID 178499251, compound

HRID 1189986Notes

Reaction equation

HRID 1189986 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-37d81728de4b41a8bb67eb7cb5c979a8
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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