Sodium Hydroxide → HCID 67216716, compound

HRID 446973Notes

Reaction equation

HRID 446973 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].[OH-].[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 14798Sodium HydroxideHCID 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 101.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 14 (923 mg, 2.28 mmol) in MeOH (20 mL) was treated with 1M NaOH (7.8 mL) at ambient temperature. After 1.5 h, the solution was concentrated and diluted with EtOAc and 1M HCl. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic extracts were washed successively with 1M HCl, and brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 36 as a yellow-colored foam (900 mg) which was used without further purification. Mass spectrum, m/z [391.4] (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc and 1M HCl
  3. customThe layers were separated
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washThe combined organic extracts were washed successively with 1M HCl, and brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-bc57a267667f48b19f8b955836ad8502
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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