Trifluoroacetic acid → HCID 68776188, compound

HRID 2069160Notes

Reaction equation

HRID 2069160 reaction equation
[ClH:1].CC(C)([O:5][C:6](=[O:45])[CH2:7][NH:8][C@@H:9]([C:23]([N:25]1[CH2:44][CH2:43][CH2:42][C@H:26]1[C:27]([NH:29][CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37]([NH2:41])=[N:36][CH:35]=[CH:34]2)=[O:28])=[O:24])[CH:10]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)C.FC(F)(F)C(O)=O>ClCCl>[ClH:1].[C:6]([CH2:7][NH:8][C@@H:9]([C:23]([N:25]1[CH2:44][CH2:43][CH2:42][C@H:26]1[C:27]([NH:29][CH2:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[C:37]([NH2:41])=[N:36][CH:35]=[CH:34]2)=[O:28])=[O:24])[CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([OH:45])=[O:5]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68777810HCID 68777810, compound

Product 1

HCID 68776188HCID 68776188, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(1,1-dimethylethoxy)-2-oxoethyl]-β-phenyl-D-phenylalanyl-N-[(1-amino-6-isoquinolyl)methyl]-L-prolinamide hydrochloride c (4.6 g, 7.1 mmol) in dichloromethane (25 ml) was added trifluoroacetic acid (4.6 ml). After standing over-night the solution was evaporated to dryness, dissolved in dichloromethane and excess hydrochloric acid in diethyl ether added. The product was precipitated by addition of anhydrous diethyl ether then collected by filtration and dried under vacuum to give 2.8 g. A further 0.8 g was obtained by precipitation from the mother liquors.

Workup

  1. waitAfter standing over-night
  2. customthe solution was evaporated to dryness
  3. dissolutiondissolved in dichloromethane
  4. additionexcess hydrochloric acid in diethyl ether added
  5. customThe product was precipitated by addition of anhydrous diethyl ether
  6. filtrationthen collected by filtration
  7. customdried under vacuum
  8. customto give 2.8 g
  9. customA further 0.8 g was obtained by precipitation from the mother liquors

Sources & evidence

ORD record
ord-a2389dc3d5a54c1989757df62db91b66
Source dataset
uspto-grants-2012_10
Patent number
US08299091B2

Reaction notes

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