Sodium Methoxide → HCID 67216716, compound

HRID 446966Notes

Reaction equation

HRID 446966 reaction equation
C[O:2][C:3]([CH:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH:7]2[CH2:20][CH2:21][N:22]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:6]12)=[O:4].C[O-].[Na+]>CO>[C:26]([O:25][C:23]([N:22]1[CH:6]2[CH:7]([N:8]([C:10]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:11])[CH2:9][CH:5]2[C:3]([OH:4])=[O:2])[CH2:20][CH2:21]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67280928Hexahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester 3-methyl ester

Product 1

HCID 67216716HCID 67216716, compoundYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 25 (1.4 g, 3.5 mmol) in MeOH (20 mL) was added to a solution of NaOMe (0.34 g, 6.3 mmol) in MeOH at ambient temperature. The reaction mixture was stirred for 16 h and then concentrated. The residue was diluted with EtOAc, washed successively with 1M HCl, brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 13 as an orange-colored foam (1.39 g) that was used without further purification.

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with EtOAc
  3. washwashed successively with 1M HCl, brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-82c34970e411472690736a564dc8a0db
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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