Hydrochloric Acid → HCID 58113996, compound

HRID 401840Notes

Reaction equation

HRID 401840 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C:3]#[C:4][C:5]1[S:9][CH:8]=[C:7]([N:10]([CH:21]2[CH2:30][CH2:29][C:24]3(OCC[O:25]3)[CH2:23][CH2:22]2)[C:11]([C@@H:13]2[C@@H:18]([CH3:19])[CH2:17][C:16]([CH3:20])=[CH:15][CH2:14]2)=[O:12])[CH:6]=1.Cl>C1COCC1>[CH3:31][C:2]([CH3:1])([CH3:32])[C:3]#[C:4][C:5]1[S:9][CH:8]=[C:7]([N:10]([CH:21]2[CH2:22][CH2:23][C:24](=[O:25])[CH2:29][CH2:30]2)[C:11]([C@@H:13]2[C@@H:18]([CH3:19])[CH2:17][C:16]([CH3:20])=[CH:15][CH2:14]2)=[O:12])[CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58114143HCID 58114143, compound

Product 1

HCID 58113996HCID 58113996, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

(1S,6S)-4,6-Dimethyl-cyclohex-3-ene-carboxylic acid [5-(3,3-dimethyl-but-1-ynyl)-thiophen-3-yl]-(1,4-dioxa-spiro[4.5]dec-8-yl)-amide (5.6 g, 12 mmol) was dissolved in THF (70 mL) and treated with 4M HCl (35 mL). The reaction mixture was heated to 45° C. and stirred for 2.5 h. THF was removed in vacuo, and the aqueous layer was thrice extracted into ethyl acetate. The combined organic layers were washed with saturated NaHCO3 (aq), water, and brine, dried over MgSO4, filtered, and concentrated to give (1S,6S)-4,6-dimethyl-cyclohex-3-ene-carboxylic acid [5-(3,3-dimethyl-but-1-ynyl)-thiophen-3-yl]-(4-oxo-cyclohexyl)-amide (5.05 g, 12 mmol).

Workup

  1. customTHF was removed in vacuo
  2. extractionthe aqueous layer was thrice extracted into ethyl acetate
  3. washThe combined organic layers were washed with saturated NaHCO3 (aq), water, and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d959638c0c64ef6a6f09ee066b15e72
Source dataset
uspto-grants-2014_06
Patent number
US08741946B2

Reaction notes

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