Hydrochloric Acid → HCID 71269874, compound

HRID 401837Notes

Reaction equation

HRID 401837 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([O:12]C)=[O:11])=[C:7]([N:14]([CH:24]([CH3:26])[CH3:25])[C:15]([C@H:17]2[CH2:22][CH2:21][C:20]([CH3:23])=[CH:19][CH2:18]2)=[O:16])[CH:6]=1.O.[OH-].[Li+].Cl>C1COCC1.CO>[CH3:1][C:2]([CH3:27])([CH3:28])[C:3]#[C:4][C:5]1[S:9][C:8]([C:10]([OH:12])=[O:11])=[C:7]([N:14]([CH:24]([CH3:25])[CH3:26])[C:15]([C@H:17]2[CH2:22][CH2:21][C:20]([CH3:23])=[CH:19][CH2:18]2)=[O:16])[CH:6]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 71230545HCID 71230545, compound

Product 1

HCID 71269874HCID 71269874, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-Methyl 5-(3,3-dimethylbut-1-ynyl)-3-(N-isopropyl-4-methylcyclohex-3-enecarboxamido)thiophene-2-carboxylate (123 mg, 0.31 mmol) was dissolved in THF (2 mL). Water (0.5 mL), methanol (0.5 mL) and lithium hydroxide (129 mg, 3.1 mmol) were added. The mixture was sealed and heated to 45 deg C. for 30 min. After an additional 1 h at ambient temperature, the mixture was treated with 10% HCl (until the pH was less than 3) and partitioned between water and ethyl acetate. The organic layer was separated, dried over sodium sulfate (anhyd) and the residue was purified by reverse phase HPLC to give the title compound, 41 mg (35% yield): MS (m/z): 388.0 [M+H]+; HPLC retention time 4.59 min (2-98% acetonitrile: water with 0.05% trifluoroacetic acid).

Workup

  1. customThe mixture was sealed
  2. temperatureheated to 45 deg C
  3. waitAfter an additional 1 h at ambient temperature
  4. custompartitioned between water and ethyl acetate
  5. customThe organic layer was separated
  6. dry with materialdried over sodium sulfate (anhyd)
  7. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0bc8d17009a84d9c93ae739bca3d8d29
Source dataset
uspto-grants-2014_06
Patent number
US08741946B2

Reaction notes

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