Trifluoroacetic acid → benzyl (S)-1-[(1S,2R,4R)-4-amino-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate

HRID 1374286Notes

Reaction equation

HRID 1374286 reaction equation
[CH2:1]([O:8][C:9](=[O:34])[NH:10][C@H:11]1[CH2:15][CH2:14][N:13]([C@H:16]2[CH2:21][CH2:20][C@@H:19]([NH:22]C(OC(C)(C)C)=O)[CH2:18][C@H:17]2[CH2:30][CH2:31][CH3:32])[C:12]1=[O:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:22][C@@H:19]1[CH2:20][CH2:21][C@H:16]([N:13]2[CH2:14][CH2:15][C@H:11]([NH:10][C:9](=[O:34])[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:12]2=[O:33])[C@H:17]([CH2:30][CH2:31][CH3:32])[CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68767765HCID 68767765, compound

Product 1

HCID 86596857benzyl (S)-1-[(1S,2R,4R)-4-amino-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(3S)-1-[(1S,2R,4R)-4-tert-butoxycarbonylamino-2-propyl-cyclohexyl]-2-oxo-pyrrolidin-3-yl}-carbamic acid benzyl ester (3.88 g, 8.2 mmol) in CH2Cl2 (90 mL) was added TFA (45 mL) at RT. The reaction was stirred for 5 h and concentrated in vacuo. The residue was partitioned between 1N NaOH (100 mL) and EtOAc (150 mL). The aqueous layer was extracted with EtOAc (2×50 mL) and the organic phases were combined, washed with brine (25 mL), dried (Na2SO4), filtered, and concentrated in vacuo to give benzyl (S)-1-[(1S,2R,4R)-4-amino-2-propylcyclohexyl]-2-oxopyrrolidin-3-ylcarbamate. MS found: (M+H)+=374.3.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1N NaOH (100 mL) and EtOAc (150 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f396341ffb8c4994a0eaaeb03eb2dd21
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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