Hydrochloric Acid → HCID 178499251, compound

HRID 1675533Notes

Reaction equation

HRID 1675533 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

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) is dissolved in tetrahydrofuran (100 mL) and treated with 3N HCl solution (50 mL). The reaction is stirred at 40° C. for 3 h. The reaction mixture is evaporated under reduced pressure. The residue is dissolved in EtOAc and washed with aq. sat. NaHCO3 solution. The organic layer is 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 is evaporated under reduced pressure
  2. dissolutionThe residue is dissolved in EtOAc
  3. washwashed with aq. sat. NaHCO3 solution
  4. customThe organic layer is separated
  5. customdried on Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a7cc08fff0514e4aadfa0bbea7ac34aa
Source dataset
uspto-grants-2011_08
Patent number
US08003685B2

Reaction notes

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