Trifluoroacetic acid → {2-[4-(2-Amino-3,3-dimethyl-butyryl)-3-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl ester

HRID 446991Notes

Reaction equation

HRID 446991 reaction equation
C(OC(=O)[NH:7][CH:8]([C:13]([N:15]1[CH2:19][CH2:18][CH:17]2[N:20]([C:36](=[O:49])[CH2:37][NH:38][C:39]([O:41][CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[O:40])[CH2:21][CH:22]([C:23](=[O:35])[NH:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[CH:16]12)=[O:14])[C:9]([CH3:12])([CH3:11])[CH3:10])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:42]([O:41][C:39](=[O:40])[NH:38][CH2:37][C:36]([N:20]1[CH2:21][CH:22]([C:23](=[O:35])[NH:24][C:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:28]=[CH:27][CH:26]=2)[CH:16]2[N:15]([C:13](=[O:14])[CH:8]([NH2:7])[C:9]([CH3:10])([CH3:11])[CH3:12])[CH2:19][CH2:18][CH:17]12)=[O:49])[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67282206{1-[4-(2-Benzyloxycarbonylamino-acetyl)-6-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid tert-butyl ester

Product 1

HCID 67281524{2-[4-(2-Amino-3,3-dimethyl-butyryl)-3-(naphthalen-1-ylcarbamoyl)-hexahydro-pyrrolo[3,2-b]pyrrol-1-yl]-2-oxo-ethyl}-carbamic acid benzyl esterYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 57 (570 mg) in DCM (10 mL) was treated with TFA (3 mL) at ambient temperature. After 2 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 58 (450 mg) which was used without further purification. Mass spectrum, m/z [586.4] (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-8a14be68781b431096f6b0c4b001e8f6
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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