Sodium Methoxide → Hexahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester

HRID 1965204Notes

Reaction equation

HRID 1965204 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 67216716Hexahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl esterYield 101.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 74 (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 72 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-44592de128dd499eae214d4d038f00f3
Source dataset
uspto-grants-2013_04
Patent number
US08415486B2

Reaction notes

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