Acetic Acid → HCID 66684819, compound

HRID 579195Notes

Reaction equation

HRID 579195 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][C:13](=O)[CH2:12][CH:11]1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:4].[BH3-]C#[N:32].[Na+].CC(O)=O>CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][CH:13]([NH2:32])[CH2:12][CH:11]1[CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 66684402HCID 66684402, compound

Product 1

HCID 66684819HCID 66684819, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2-cyclohexyl-4,6-dioxo-piperidin-1-yl)-5-phenyl-thiophene-2-carboxylic acid methyl ester (400 mg, 0.98 mmol, 1.0 equiv) in MeOH (2.0 mL) was added NH4OAc (375 mg, 4.86 mmol, 5 equiv) and the resulting solution was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the residue was dissolved MeOH. To the solution was added NaCNBH3 (247 mg, 1.16 mmol, 1.2 equiv) and HOAc (56 mg, 0.97 mmol, 1 equiv). The resulting mixture was stirred at room temperature for 18 hours. The solvent was then removed in vacuo. To the residue was added sat. aq. NaHCO3 solution until pH>8. The mixture was extracted with DCM. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude material was continued to the next step with no further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved MeOH
  3. stirringThe resulting mixture was stirred at room temperature for 18 hours
  4. customThe solvent was then removed in vacuo
  5. additionTo the residue was added sat. aq. NaHCO3 solution until pH>8
  6. extractionThe mixture was extracted with DCM
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe crude material was continued to the next step with no further purification

Sources & evidence

ORD record
ord-c71b420827054d98901f7965256e552c
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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