Trifluoroacetic acid → 4-(2-Amino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

HRID 446959Notes

Reaction equation

HRID 446959 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:23](=[O:39])[CH:24]([NH:31]C(OC(C)(C)C)=O)[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[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][N:22]([C:23](=[O:39])[CH:24]([NH2:31])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:6]12)=[O:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 672814894-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

Product 1

HCID 672816724-(2-Amino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl esterYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 16 (346 mg, 0.64 mmol) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 1 h, the solution was concentrated, diluted with EtOAc, and washed with saturated NaHCO3. The aqueous phase was back extracted with DCM and the combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford 17 (245 mg) as an orange-colored foam that was used without further purification. Mass spectrum, m/z [444.4] (M+H)+.

Workup

  1. concentrationthe solution was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3
  4. extractionThe aqueous phase was back extracted with DCM
  5. washthe combined organic extracts were washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-064124e6be2c474793d1561fa328825b
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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