Trifluoroacetic acid → HCID 86596975, compound

HRID 2225308Notes

Reaction equation

HRID 2225308 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18]C(=O)OC(C)(C)C)[CH2:14][C@H:13]1[C:26]1[O:30][N:29]=[C:28]([CH3:31])[N:27]=1)=[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>[NH2:18][C@@H:15]1[CH2:16][CH2:17][C@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:13]([C:26]2[O:30][N:29]=[C:28]([CH3:31])[N:27]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86596976HCID 86596976, compound

Product 1

HCID 86596975HCID 86596975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To absolution of tert-butyl (1R,3R,4S)-4-((benzyloxycarbonyl)amino)-3-(3-methyl-1,2,4-oxadiazol-5-yl)cyclohexylcarbamate (250 mg) in CH2Cl2 (10 mL) was added TFA (3 mL) at RT. The reaction was stirred for 5 h and concentrated in vacuo. The residue was partitioned between 1N NaOH (30 mL) and EtOAc (40 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 (1S,2R,4R)-4-amino-2-(3-methyl-1,2,4-oxadiazol-5-yl)cyclohexylcarbamate. MS found: (M+H)+=331.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between 1N NaOH (30 mL) and EtOAc (40 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-3a4d4668efb64ee4b92c21435d48cb5f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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