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

HRID 413221Notes

Reaction equation

HRID 413221 reaction equation
C([O:5][C:6](=[O:43])[C@@H:7]([NH:28][C:29]([O:31][CH2:32][C:33]12[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[CH2:34]1)[CH2:40]2)=[O:30])[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]([CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]2[NH:22][CH2:23][CH2:24][CH2:25][N:26]=2)=[CH:15][CH:16]=1)=[O:11])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:33]12([CH2:32][O:31][C:29]([NH:28][C@@H:7]([CH2:8][NH:9][C:10]([C:12]3[S:13][C:14]([CH2:17][CH2:18][C:19](=[O:27])[NH:20][C:21]4[NH:22][CH2:23][CH2:24][CH2:25][N:26]=4)=[CH:15][CH:16]=3)=[O:11])[C:6]([OH:43])=[O:5])=[O:30])[CH2:42][CH:37]3[CH2:38][CH:39]([CH2:41][CH:35]([CH2:36]3)[CH2:34]1)[CH2:40]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69637241(2s)-2-(1-Adamantylmethoxycarbonylamino)-3-((5-(2-(1,4,5,6-tetrahydropyrimidin-2-ylcarbamoyl)-ethyl)-thiophene-2-carbonyl)-amino)-propionic acid tert-butyl ester

Product 1

HCID 10415384(S)-2-(Adamantan-1-ylmethoxycarbonylamino)-3-{[5-(3-guanidino-3-oxo-propyl)-thiophene-2-carbonyl]-amino}-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

117 mg (0.19 mmol) of the product obtained in step c) were dissolved in 5 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, and the residue was dissolved in acetic acid and again evaporated to dryness. This procedure was repeated once. The resinous residue was triturated with diethyl ether. After filtration 90 mg of a colourless amorphous powder were obtained.

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionthe residue was dissolved in acetic acid
  3. customagain evaporated to dryness
  4. customThe resinous residue was triturated with diethyl ether
  5. filtrationAfter filtration 90 mg of a colourless amorphous powder
  6. customwere obtained

Sources & evidence

ORD record
ord-b556143f01c244fbad846c6cfa134994
Source dataset
uspto-grants-2003_05
Patent number
US06566366B1

Reaction notes

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