Trifluoroacetic acid → HCID 58204944, compound

HRID 1629418Notes

Reaction equation

HRID 1629418 reaction equation
FC(F)(F)C(O)=O.[CH:8]([N:11]1[C:15]([C:16]2[N:17]=[C:18]3[C:24]4[CH:25]=[CH:26][C:27]([N:29]5[CH2:33][CH2:32][CH2:31][C@H:30]5[C:34]([O:36]C(C)(C)C)=[O:35])=[CH:28][C:23]=4[O:22][CH2:21][CH2:20][N:19]3[CH:41]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9].C([SiH](CC)CC)C>ClCCl>[CH:8]([N:11]1[C:15]([C:16]2[N:17]=[C:18]3[C:24]4[CH:25]=[CH:26][C:27]([N:29]5[CH2:33][CH2:32][CH2:31][C@H:30]5[C:34]([OH:36])=[O:35])=[CH:28][C:23]=4[O:22][CH2:21][CH2:20][N:19]3[CH:41]=2)=[N:14][CH:13]=[N:12]1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 58204577HCID 58204577, compound

Product 1

HCID 58204944HCID 58204944, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a mixture of 153 mg of (S)-tert-butyl 1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)pyrrolidine-2-carboxylate and 0.2 ml of triethylsilane in 5 ml of dichloromethane. The reaction mixture was stirred for 3 hours. The mixture was concentrated, the residue partitioned between 1 M aq. Na2CO3 and ethyl ether. The aqueous layer was extracted with ethyl acetate two more times. The organic layers were discarded, the aqueous solution neutralized to pH 6. A precipitate was collected, washed with water, dried in high vacuum for 36 hours to give (S)-1-(2-(1-isopropyl-1H-1,2,4-triazol-5-yl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-9-yl)pyrrolidine-2-carboxylic acid. Yield 55 mg. M/z 409.3, calc. 408.19

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between 1 M aq. Na2CO3 and ethyl ether
  3. extractionThe aqueous layer was extracted with ethyl acetate two more times
  4. customA precipitate was collected
  5. washwashed with water
  6. customdried in high vacuum for 36 hours

Sources & evidence

ORD record
ord-3df89758eed5401aaf5fe7e4982dfa3e
Source dataset
uspto-grants-2014_07
Patent number
US08785626B2

Reaction notes

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