Acetaldehyde → HCID 86696906, compound

HRID 1399995Notes

Reaction equation

HRID 1399995 reaction equation
C[O-].[Na+].C(OP([CH2:12][C:13]1[N:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)[C:22]3[S:26][C:25]([NH:27][C:28]([NH:30][CH2:31][CH3:32])=[O:29])=[N:24][C:23]=3[CH:33]=2)=[CH:15][N:14]=1)(OCC)=O)C.[CH:40](=O)[CH3:41]>C1COCC1.CCOC(C)=O>[CH2:31]([NH:30][C:28]([NH:27][C:25]1[S:26][C:22]2[C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=3)=[CH:20][C:19]([C:16]3[CH:15]=[N:14][C:13](/[CH:12]=[CH:40]/[CH3:41])=[N:18][CH:17]=3)=[CH:33][C:23]=2[N:24]=1)=[O:29])[CH3:32]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 10942334Sodium MethoxideHCID 86696904HCID 86696904, compound

Product 1

HCID 86696906HCID 86696906, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium methoxide (0.5 M MeOH solution; 0.9 mL, 0.43 mmol) was added drop-wise to a suspension of iv (104 mg, 0.198 mmol) in THF (10 mL). Acetaldehyde (40 μL, 0.69 mmol) was introduced and the mixture stirred for 90 min. The reaction was diluted with EtOAc (60 mL), washed with sat. NaHCO3(aq) (60 mL). The organic fraction was dried (MgSO4), concentrated in vacuo, and purified over silica (gradient elution: 0-10%, DCM-MeOH) affording v (79 mg, 96%). MS: 417.1 [M+H]+.

Workup

  1. washwashed with sat. NaHCO3(aq) (60 mL)
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified over silica (gradient elution: 0-10%, DCM-MeOH)
  5. customaffording v (79 mg, 96%)

Sources & evidence

ORD record
ord-b48ad60cd4b147c0902fa90a9426cad5
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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