Trifluoroacetic acid → HCID 23554373, compound

HRID 133304Notes

Reaction equation

HRID 133304 reaction equation
C(OC([NH:8][C@H:9]([C:11]([NH:13][CH:14]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=2[N:16]([CH3:31])[C:15]1=[O:32])=[O:12])[CH3:10])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:8][C@H:9]([C:11]([NH:13][CH:14]1[N:20]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=2[N:16]([CH3:31])[C:15]1=[O:32])=[O:12])[CH3:10]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23554394HCID 23554394, compound

Product 1

HCID 23554373HCID 23554373, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[(N-tert-butoxycarbonyl-L-alaninyl)amino]-2,3-dihydro-1-methyl-5-(2-pyridyl)-1H-1,4-benzodiazepin-2-one (3.42 g, 7.82 mmol) in CH2Cl2 (90 mL) was cooled in an ice bath and treated with TFA (13.2 mL, 172 mmol). The cold bath was removed and the solution stirred at room temperature for four hours. The reaction mixture was washed with 1 M aq. K2CO3 and the aqueous back-extracted with CH2Cl2. The combined extracts were washed with H2O, dried (MgSO4) and concentrated to obtain 1.75 g (66% yield) of the title compound as an off-white foam. MS (IS+) 338 (m/e).

Workup

  1. customThe cold bath was removed
  2. washThe reaction mixture was washed with 1 M aq. K2CO3
  3. extractionthe aqueous back-extracted with CH2Cl2
  4. washThe combined extracts were washed with H2O
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a5dc2e27439e4855805c24dd3efcd669
Source dataset
uspto-grants-2008_06
Patent number
US07390801B2

Reaction notes

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