Trifluoroacetic acid → (S)-2-(Adamantan-1-ylmethoxycarbonylamino)-3-{[5-(2-guanidinocarbonyl-cyclopropyl)-thiophene-2-carbonyl]-amino}-propionic acid

HRID 413218Notes

Reaction equation

HRID 413218 reaction equation
C([O:5][C:6](=[O:44])[C@@H:7]([NH:29][C:30]([O:32][CH2:33][C:34]12[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]3)[CH2:35]1)[CH2:41]2)=[O:31])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH:17]2[CH2:19][CH:18]2[C:20](=[O:28])[NH:21][C:22]2[NH:23][CH2:24][CH2:25][CH2:26][N:27]=2)=[CH:15][CH:16]=1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:34]12([CH2:33][O:32][C:30]([NH:29][C@@H:7]([CH2:8][NH:9][C:10]([C:12]3[S:13][C:14]([CH:17]4[CH2:19][CH:18]4[C:20](=[O:28])[NH:21][C:22]4[NH:23][CH2:24][CH2:25][CH2:26][N:27]=4)=[CH:15][CH:16]=3)=[O:11])[C:6]([OH:44])=[O:5])=[O:31])[CH2:43][CH:38]3[CH2:39][CH:40]([CH2:42][CH:36]([CH2:37]3)[CH2:35]1)[CH2:41]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69637307(2s)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-cyclopropyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

Product 1

HCID 15859414(S)-2-(Adamantan-1-ylmethoxycarbonylamino)-3-{[5-(2-guanidinocarbonyl-cyclopropyl)-thiophene-2-carbonyl]-amino}-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

48 mg of the product obtained in step c) were dissolved in 2 ml of dichloromethane and stirred for 3 hours with 1 ml of trifluoroacetic acid under an inert gas atmosphere at room temperature. The solvents were removed in vacuo, the residue was dissolved in acetic acid and the solution was again evaporated to dryness. This procedure was repeated once. The resinous residue was triturated with diethyl ether. After filtration 30 mg of the title compound were obtained as a colourless amorphous powder.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in acetic acid
  3. customthe solution was again evaporated to dryness
  4. customThe resinous residue was triturated with diethyl ether
  5. filtrationAfter filtration 30 mg of the title compound
  6. customwere obtained as a colourless amorphous powder

Sources & evidence

ORD record
ord-aa151016de1340bbbd73b29089fcaf18
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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