Trifluoroacetic acid → HCID 24946975, compound

HRID 1675529Notes

Reaction equation

HRID 1675529 reaction equation
C(OC([N:8]([CH2:22]/[CH:23]=[CH:24]/[C:25]1[CH:30]=[CH:29][C:28]([C:31]2[S:32][C:33]([NH:39][C:40](=[O:42])[NH2:41])=[C:34]([C:36](=[O:38])[NH2:37])[CH:35]=2)=[CH:27][CH:26]=1)[C@H:9]([C:14]([O:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.FC(F)(F)C(O)=O.CCCC(C)C>ClCCl>[C:36]([C:34]1[CH:35]=[C:31]([C:28]2[CH:27]=[CH:26][C:25](/[CH:24]=[CH:23]/[CH2:22][NH:8][C@H:9]([C:14]([O:16][CH:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[O:15])[CH2:10][CH:11]([CH3:12])[CH3:13])=[CH:30][CH:29]=2)[S:32][C:33]=1[NH:39][C:40](=[O:42])[NH2:41])(=[O:38])[NH2:37]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 78922-MethylpentaneHCID 67345783HCID 67345783, compound2×

Product 1

HCID 24946975HCID 24946975, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of cyclopentyl N-(tert-butoxycarbonyl)-N-[(2E)-3-{-4-[4-carbamoyl-5-(carbamoylamino)thiophen-2-yl]phenyl}prop-2-en-1-yl]-leucinate (Intermediate 9a) (39 mg, 0.065 mmol) in dichloromethane (1 ml) was added trifluoroacetic acid (0.5 ml). The reaction mixture was left to stir at RT for 2 hrs. The reaction mixture was worked up by removal of the solvents in vacuo. The residue was diluted with methanol and captured by SCX chromatography, eluting the product with ammonia in methanol. The ammonia fractions were concentrated in vacuo to afford an oily residue. This was taken up in dichloromethane and isohexane added. After removal of the solvent in vacuo a pale orange solid was obtained (24.3 mg, 0.049 mmol, 75%).

Workup

  1. waitThe reaction mixture was left
  2. customThe reaction mixture was worked up by removal of the solvents in vacuo
  3. additionThe residue was diluted with methanol
  4. washeluting the product with ammonia in methanol
  5. concentrationThe ammonia fractions were concentrated in vacuo
  6. customto afford an oily residue
  7. customAfter removal of the solvent in vacuo a pale orange solid
  8. customwas obtained (24.3 mg, 0.049 mmol, 75%)

Sources & evidence

ORD record
ord-9682492bab744495b4588fec80b643a3
Source dataset
uspto-grants-2011_08
Patent number
US08003695B2

Reaction notes

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