Trifluoroacetic acid → Hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

HRID 446957Notes

Reaction equation

HRID 446957 reaction equation
[CH3:1][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(OC(C)(C)C)=O)[CH:6]12)=[O:4].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11])[CH:7]2[CH2:20][CH2:21][NH:22][CH:6]12)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67280928Hexahydro-pyrrolo[3,2-b]pyrrole-1,3,4-tricarboxylic acid 1-benzyl ester 4-tert-butyl ester 3-methyl ester

Product 1

HCID 67281633Hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl esterYield 84.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14 (480 mg, 1.2 mmol) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 75 min, the solution was concentrated, diluted with EtOAc, washed with saturated NaHCO3, brine. The aqueous washes were back extracted with DCM and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to afford crude 15 (309 mg) as an orange-colored oil that was used without further purification. Mass spectrum, m/z [305.2] (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3, brine
  4. extractionThe aqueous washes were back extracted with DCM
  5. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-6ef2bc5538c34524bf28d7f1f20d9a95
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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