Benzenepropanoic acid, alpha-(phenylmethyl)- → HCID 178456021, compound

HRID 1655753Notes

Reaction equation

HRID 1655753 reaction equation
[NH2:1][C@@H:2]([CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)[C:3]([NH:5][C@@H:6]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@@H:7]([OH:15])[CH2:8][CH:9]([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH2:11])=[O:4].C(N(C(C)C)C(C)C)C.[CH2:35]([CH:42]([CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[C:43](O)=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(#N)C>[CH2:46]([CH:42]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:43]([NH:1][C@@H:2]([CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)[C:3]([NH:5][C@@H:6]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@@H:7]([OH:15])[CH2:8][C@@H:9]([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH2:11])=[O:4])=[O:44])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

6

Reactant 4

HCID 64800Benzenepropanoic acid, alpha-(phenylmethyl)-HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178446065HCID 178446065, compound

Product 1

HCID 178456021HCID 178456021, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

0.65 g of (S)-α-amino-N-[(1S,2S,4RS)-2-hydroxy-1-isobutyl-4-isopropyl-5-hexenyl]imidazole-4-propionamide in 20 ml of acetonitrile were added together with 0.36 ml of ethyldiisopropylamine to a solution of 0.45 g of 2-benzyl-3-phenylpropionic acid (which was prepared according to the method described in J. Am. Chem. Soc. 71 1863 (1949)) and 0.8 g of BOP in 30 ml of acetonitrile and the mixture was stirred at room temperature for 20 hours. Subsequently, the reaction mixture was evaporated under reduced pressure, the residue was dissolved in 50 ml of ethyl acetate and the organic solution was washed twice with 100 ml of water each time, dried over sodium sulfate and evaporated. The residue Was separated by flash chromatography on 100 g of silica gel with a 250:15 mixture of methylene chloride and methanol as the eluting agent, to obtain there was obtained 0.17 g of (S)-α-(2,2-dibenzylacetamido)-N-[(1S,2S,4S)-2 -hydroxy-1-isobutyl-4-isopropyl-5-hexenyl]imidazole-4-propionamide as a white powder, melting point 120°. This compound corresponds to the less polar isomer and has a Rf value of 0.14.

Workup

  1. customwas prepared
  2. customSubsequently, the reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in 50 ml of ethyl acetate
  4. washthe organic solution was washed twice with 100 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue Was separated by flash chromatography on 100 g of silica gel with a 250:15 mixture of methylene chloride and methanol as the eluting agent
  8. customto obtain there

Sources & evidence

ORD record
ord-20a617a9d05e44588da6ea7e785d39ed
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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