Trifluoroacetic acid → HCID 178448271, compound

HRID 847322Notes

Reaction equation

HRID 847322 reaction equation
[C:1]([C@H:9]([CH:56]([CH3:58])[CH3:57])[CH2:10][C@H:11]([OH:55])[C@@H:12]([NH:20][C:21](=[O:54])[C@@H:22]([NH:36][C:37](=[O:53])[C@@H:38]([CH2:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:23][C:24]1[N:25](C(OC(C)(C)C)=O)[CH:26]=[N:27][CH:28]=1)[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:1]([C@H:9]([CH:56]([CH3:58])[CH3:57])[CH2:10][C@H:11]([OH:55])[C@@H:12]([NH:20][C:21](=[O:54])[C@@H:22]([NH:36][C:37](=[O:53])[C@@H:38]([CH2:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:23][C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 22845455HCID 22845455, compound

Product 1

HCID 178448271HCID 178448271, compoundYield 24.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.4 g (0.5 mmol) of (S)-N-[(1S,2S,4S)-4-benzoyl-1-(cyclohexylmethyl)-2-hydroxy-5-methylhexyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl)hydrocinnamamido]-3-t-butoxycarbonylimidazole-4-propionamide is dissolved in 5 ml of methylene chloride and treated with 2 ml of 90% trifluoroacetic acid and stirred at room temperature for 4 hours. Thereafter, the reaction mixture is poured into 2N sodium bicarbonate solution and extracted with methylene chloride. The methylene chloride extracts are dried over potassium carbonate and evaporated under reduced pressure. Chromatography of the residue on 8 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent yields 0.087 g of (S)-N-[(1S,2S,4S)-4-benzoyl-1-(cyclohexylmethyl)-2-hydroxy-5-methylhexyl]-α-[(R)-α-(3,3-dimethyl-2-oxobutyl]hyrocinnamamido]imidazole-4-propionamide as an amorphous solid, MS: 699 (M+H)+.

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe methylene chloride extracts are dried over potassium carbonate
  3. customevaporated under reduced pressure
  4. additionChromatography of the residue on 8 g of silica gel with a mixture of methylene chloride and isopropanol as the eluting agent

Sources & evidence

ORD record
ord-21a6f15691b340cabf494f7d0be95792
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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