Trifluoroacetic acid methylene chloride → HCID 23554372, compound

HRID 1835892Notes

Reaction equation

HRID 1835892 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-dbf0f55c61fd4b49942d404a04c9edf1
Source dataset
uspto-grants-2004_08
Patent number
US06774125B2

Reaction notes

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