Trifluoroacetic acid methylene chloride → HCID 23554370, compound

HRID 2121519Notes

Reaction equation

HRID 2121519 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-b33b4a8a40244100a0784acb6e6ce67f
Source dataset
uspto-grants-2004_02
Patent number
US06696438B2

Reaction notes

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