Trifluoroacetic acid methylene chloride → HCID 68442018, compound

HRID 2389862Notes

Reaction equation

HRID 2389862 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:10]2[CH2:11][N:12](C(OC(C)(C)C)=O)[CH2:13][C:9]=2[C:8]([NH:21][C:22](=[O:35])[CH:23]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[CH3:24])=[N:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)Cl>C(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[C:10]2[CH2:11][NH:12][CH2:13][C:9]=2[C:8]([NH:21][C:22](=[O:35])[CH:23]([C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[CH3:24])=[N:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 684415245-(1,1-Dimethylethyl) 1-ethyl 4,6-dihydro-3-[[2-(2-naphthalenyl)-1-oxopropyl]amino]pyrrolo[3,4-c]pyrazole-1,5-dicarboxylate

Product 1

HCID 68442018HCID 68442018, compoundYield 101.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.5 g (5.2 mmol) of 3-(2-naphthalen-2-yl-propionylamino)-4,6-dihydro-pyrrolo[3,4-c]pyrazole-1,5-dicarboxylic acid 5-tert-butyl ester 1-ethyl ester in 15 ml DCM was treated with 16 ml of (1:1) TFA/DCM. The reaction mixture was stirred for 30 min. and evaporated to dryness. The resulting residue was dissolved in DCM and the solution was washed with brine and then treated with NaHCO3 aq. The obtained precipitate was filtered, washed with water and DCM, and then dried under vacuum to give 2.0 g (quantitative yield) of the title compound.

Workup

  1. customevaporated to dryness
  2. dissolutionThe resulting residue was dissolved in DCM
  3. washthe solution was washed with brine
  4. additiontreated with NaHCO3 aq. The obtained precipitate
  5. filtrationwas filtered
  6. washwashed with water and DCM
  7. customdried under vacuum

Sources & evidence

ORD record
ord-cf5f911e951c42d29a6a8a00c526dc66
Source dataset
uspto-grants-2012_09
Patent number
US08273765B2

Reaction notes

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