Sodium Methoxide → HCID 66850788, compound

HRID 386754Notes

Reaction equation

HRID 386754 reaction equation
[CH3:1][O:2][C:3](=[O:35])[CH2:4][C:5]([N:7]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=1)[C:8]1[CH2:12][N:11]([C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:10][C:9]=1[C:19]([O:21]CC)=O)=[O:6].C[O-].[Na+]>CO>[OH:21][C:19]1[C:9]2[CH2:10][N:11]([C:13](=[O:18])[CH2:14][CH2:15][CH:16]=[CH2:17])[CH2:12][C:8]=2[N:7]([CH2:24][C:25]2[CH:26]=[CH:27][C:28]([C:31]([F:33])([F:34])[F:32])=[CH:29][CH:30]=2)[C:5](=[O:6])[C:4]=1[C:3]([O:2][CH3:1])=[O:35]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 66850664HCID 66850664, compound2×

Product 1

HCID 66850788HCID 66850788, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the product of Step B, 4-b, (6.30 g, 12.7 mmol) in MeOH (50 mL) was added NaOMe (4.35 mL, 19.0 mmol, 25 wt % in MeOH) at rt. After about 15 min the reaction was concentrated and the residue was diluted with EtOAc and washed with aq HCl (2 M) and brine. The material was crystallized from EtOAc and hexane to afford the title compound, 4-1. HPLC/MS: 451.0 (M+1); Rt=3.33 min.

Workup

  1. concentrationAfter about 15 min the reaction was concentrated
  2. additionthe residue was diluted with EtOAc
  3. washwashed with aq HCl (2 M) and brine
  4. customThe material was crystallized from EtOAc and hexane

Sources & evidence

ORD record
ord-245e03594003406c9c6d419cfc0e51d7
Source dataset
uspto-grants-2013_02
Patent number
US08372863B2

Reaction notes

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