Trifluoroacetic acid → HCID 21088239, compound

HRID 351375Notes

Reaction equation

HRID 351375 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C@H:15]2[CH2:20][CH2:19][C@@H:18]([N:21]=[N+:22]=[N-:23])[CH2:17][C@H:16]2[CH2:24][S:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[O:27])=[O:26])[C:9]1=[O:34])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C([O-])(O)=O.[Na+].CCOC(C)=O>[NH2:7][C@H:8]1[CH2:14][CH2:13][CH2:12][CH2:11][N:10]([C@H:15]2[CH2:20][CH2:19][C@@H:18]([N:21]=[N+:22]=[N-:23])[CH2:17][C@H:16]2[CH2:24][S:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)(=[O:26])=[O:27])[C:9]1=[O:34]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86594362HCID 86594362, compound

Product 1

HCID 21088239HCID 21088239, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of [(3S)-1-(1S,2R,4R)-(4-azido-2-benzenesulfonylmethyl-cyclohexyl)-2-oxo-azepan-3-yl]-carbamic acid tert-butyl ester (120 mg) in CH2Cl2 (10 mL) was added TFA (3.3 mL). After 45 min, the solution was diluted with NaHCO3 solution (aq) and EtOAc. The organic layer was collected, dried, and concentrated to afford to a crude oil 3-amino-(3S)-1-(1S,2R,4R)-(4-azido-2-benzenesulfonylmethyl-cyclohexyl)-azepan-2-one. MS [M+H]+=406.

Workup

  1. customThe organic layer was collected
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-7b356219e1394cdebf85a226d0111227
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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