HCID 178418546, compound → HCID 178455620, compound

HRID 2294737Notes

Reaction equation

HRID 2294737 reaction equation
[C:1]([S:5]([CH2:8][C@@H:9]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][C:37]=1I)[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[OH:20])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2].[Cu][C:47]#[N:48]>CN(C)C=O>[C:1]([S:5]([CH2:8][C@@H:9]([CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:10]([NH:12][C@@H:13]([CH2:32][C:33]1[N:34]=[CH:35][NH:36][C:37]=1[C:47]#[N:48])[C:14]([NH:16][C@@H:17]([CH2:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[C@@H:18]([OH:24])[C@H:19]([CH:21]1[CH2:23][CH2:22]1)[OH:20])=[O:15])=[O:11])(=[O:7])=[O:6])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 178418546HCID 178418546, compoundHCID 178455621HCID 178455621, compound

Product 1

HCID 178455620HCID 178455620, compoundYield 13.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 335 mg (0.44 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R, 3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-5-iodoimidazole-4-propionamide and 79 mg (0.88 mmol) of copper-(I) cyanide in 25 ml of dimethylformamide is stirred at 120° overnight under argon. Subsequently, the reaction mixture is evaporated under reduced pressure, the residue is suspended in 30 ml of a 95:5 mixture of methylene chloride and methanol and filtered over Dicalite. The filtrate is evaporated and, for purification, the residue is chromatographed on 50 g of silica gel using a 160:10:1 mixture of methylene chloride, methanol and ammonia as the eluent. After precipitation from a methylene chloride-ether mixture there are obtained 40 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-5-cyanoimidazole-4-propionamide as a colourless powder; MS: 656 (M+H)+.

Workup

  1. customSubsequently, the reaction mixture is evaporated under reduced pressure
  2. additionthe residue is suspended in 30 ml of a 95:5 mixture of methylene chloride and methanol
  3. filtrationfiltered over Dicalite
  4. customThe filtrate is evaporated and, for purification
  5. customthe residue is chromatographed on 50 g of silica gel using
  6. additiona 160:10:1 mixture of methylene chloride, methanol and ammonia as the eluent
  7. customAfter precipitation from a methylene chloride-ether mixture

Sources & evidence

ORD record
ord-fd5655dc21ec4d08940c07d9b6730028
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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