Hydrochloric Acid → HCID 178499332, compound

HRID 2388271Notes

Reaction equation

HRID 2388271 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:30]#[C:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[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.O>O1CCCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:30]#[C:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[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[CH2:21][CH2:22][C:23](=[O:24])[CH2:28][CH2:29]1)=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178499327HCID 178499327, compound

Product 1

HCID 178499332HCID 178499332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

5-(3,3-Dimethyl-but-1-ynyl)-3-[(1,4-dioxa-spiro[4.5]dec-8-yl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (1 eq.) is dissolved in tetrahydrofuran and treated with 3.6 N HCl solution. The reaction is stirred at 40° C. for 5 h. Water is then added and the reaction mixture is cooled to room temperature. The reaction mixture is extracted with ethyl acetate (2×50 mL). The combined extracts are washed with 25 mL of aqueous saturated NaHCO3 and 2×50 mL of water. The organic layer is concentrated to a thick oil and 50 mL of heptane is added to the mixture to precipitate the desired compound which is filtered to give of 5-(3,3-dimethyl-but-1-ynyl)-3-[(trans-4-methyl-cyclohexanecarbonyl)-(4-oxo-cyclohexyl)-amino]-thiophene-2-carboxylic acid methyl ester.

Workup

  1. temperaturethe reaction mixture is cooled to room temperature
  2. extractionThe reaction mixture is extracted with ethyl acetate (2×50 mL)
  3. washThe combined extracts are washed with 25 mL of aqueous saturated NaHCO3 and 2×50 mL of water
  4. concentrationThe organic layer is concentrated to a thick oil and 50 mL of heptane
  5. additionis added to the mixture
  6. customto precipitate the desired compound which
  7. filtrationis filtered

Sources & evidence

ORD record
ord-ebbc79d1cf09492e8dd15c6c40bc6741
Source dataset
uspto-grants-2012_09
Patent number
US08269014B2

Reaction notes

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