Trifluoroacetic acid methylene chloride → HCID 23554370, compound

HRID 988451Notes

Reaction equation

HRID 988451 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][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:15]1=[O:40])=[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][C:32](=[O:39])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:15]1=[O:40])=[O:12])[CH3:10]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 23554391HCID 23554391, compound

Product 1

HCID 23554370HCID 23554370, compoundYield 94%

Procedure

3-(N′-(tert-Butoxycarbonyl)-L-alaninyl) amino-2,3-dihydro-1-(2-oxo-2-phenylethyl)-5-phenyl-1H-1,4-benzodiazepin-2-one (2.5 g, 4.63 mmol) was added to 100 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 150 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 (1-10% methanol/methylene chloride) gave 1.91 g (94%) of the title compound as a white foam.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 150 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-120117b11d5e40c2b5f606852132ebc9
Source dataset
uspto-grants-2003_10
Patent number
US06635632B1

Reaction notes

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