Trifluoroacetic acid → HCID 22598958, compound

HRID 2252463Notes

Reaction equation

HRID 2252463 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:21][NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH2:34][CH2:35][CH2:36][NH:37][C:38]1[NH:39][CH:40]=[CH:41][N:42]=1)[N:29]=[CH:28]2)=[O:24])[C:18]([OH:20])=[O:19])=[O:15])=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH:17]([CH2:21][NH:22][C:23]([C:25]1[CH:26]=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH2:34][CH2:35][CH2:36][NH:37][C:38]1[NH:39][CH:40]=[CH:41][N:42]=1)[N:29]=[CH:28]2)=[O:24])[C:18]([OH:20])=[O:19])=[O:15]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22598980HCID 22598980, compound

Product 1

HCID 22598958HCID 22598958, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(6-((Tert-butoxy)carbonylamino)hexanoylamino)-3-((1-(3-(imidazol-2-ylamino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic acid (0.0322 g, 0.0551 mmol) was dissolved in methylene chloride (1 mL). Trifluoroacetic acid (1 mL) was added, and the reaction was stirred for 2 h. The reaction was concentrated to an oil under high vacuum. The oil was triturated with ether. The product was filtered, washed with ether, dissolved in 50/50 acetonitrile/water, and lyophilized to give 29.9 mgs (91%) of product. ESMS: Calcd. for C23H32N8O4, 464.25. Found, 485.2 [M+H]+1 Analytical HPLC, Method B, Rt=111.02 min, Purity=97%

Workup

  1. concentrationThe reaction was concentrated to an oil under high vacuum
  2. customThe oil was triturated with ether
  3. filtrationThe product was filtered
  4. washwashed with ether
  5. dissolutiondissolved in 50/50 acetonitrile/water

Sources & evidence

ORD record
ord-4b4729e85250458c944433d0bf00d905
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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