Trifluoroacetic acid → HCID 23554373, compound

HRID 987731Notes

Reaction equation

HRID 987731 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-67a4681e5b414be6988d3e820942b1cd
Source dataset
uspto-grants-2003_10
Patent number
US06632811B2

Reaction notes

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