Trifluoroacetic acid → HCID 68767536, compound

HRID 1455440Notes

Reaction equation

HRID 1455440 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:16][CH2:15][N:14]([C@H:17]2[CH2:22][CH2:21][C@@H:20]([NH:23]C(OC(C)(C)C)=O)[CH2:19][C@H:18]2[C:31]([O:33][CH3:34])=[O:32])[C:13]1=[O:35])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:23][C@H:20]1[CH2:19][C@@H:18]([C:31]([O:33][CH3:34])=[O:32])[C@@H:17]([N:14]2[CH2:15][CH2:16][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:10])[C:13]2=[O:35])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68765533HCID 68765533, compound

Product 1

HCID 68767536HCID 68767536, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (1R,2S,5R)-methyl 2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)-5-(tert-butoxycarbonylamino)-cyclohexanecarboxylate in CH2Cl2 (10 mL) was treated with TFA (15 mL) and stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue dissolved in CH2Cl2 and washed with NaHCO3(aq), brine, and dried over MgSO4. The solution was filtered and concentrated in vacuo to give 0.75 g (59%) of (1R,2S,5R)-methyl 5-amino-2-((S)-3-(benzyloxycarbonylamino)-2-oxopyrrolidin-1-yl)cyclohexanecarboxylate as a white solid. MS found: (M+H)+=390.3.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in CH2Cl2
  3. washwashed with NaHCO3(aq), brine
  4. dry with materialdried over MgSO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-251b21d2cec94fbfaa101cd13a6f1c29
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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