Trifluoroacetic acid methylene chloride → HCID 23554372, compound

HRID 433451Notes

Reaction equation

HRID 433451 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][CH:22]=2)[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=2[N:16]([CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:15]1=[O:38])=[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][CH:22]=2)[C:18]2[CH:27]=[CH:28][CH:29]=[CH:30][C:17]=2[N:16]([CH2:31][CH2:32][CH2:33][C:34]([F:37])([F:35])[F:36])[C:15]1=[O:38])=[O:12])[CH3:10]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 23554393HCID 23554393, compound

Product 1

HCID 23554372HCID 23554372, compoundYield 68.3%

Procedure

3-(N′-(tert-Butoxycarbonyl)-L-alaninyl)amino-2,3-dihydro-1-(4,4,4-trifluorobutyl)-5-phenyl-1H-1,4-benzodiazepin-2-one (1.21 g, 2.27 mmol) was added to 50 mL of a stirring solution of 15% TFA/methylene chloride in one portion. After stirring 2 h, the reaction mixture was concentrated under reduced pressure and the residue was dissolved in 100 mL of methylene chloride. This solution was washed twice with saturated sodium bicarbonate, once with brine and then dried over sodium sulfate. Purification of the crude product using silica gel column chromatography (1-5% methanol/methylene chloride) gave 670 mg (68%) of a light pink foam.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 100 mL of methylene chloride
  3. washThis solution was washed twice with saturated sodium bicarbonate, once with brine
  4. dry with materialdried over sodium sulfate
  5. customPurification of the crude product

Sources & evidence

ORD record
ord-7db86ae15b214f6e9a8b79713f7d87e7
Source dataset
uspto-grants-2003_12
Patent number
US06667305B1

Reaction notes

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