Triethylamine → HCID 178456022, compound

HRID 1655711Notes

Reaction equation

HRID 1655711 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][C@@H:9]([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH2:11])=[O:4].[C:26]([O:30][C:31]([NH:33][C@H:34]([C:42](O)=[O:43])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:32])([CH3:29])([CH3:28])[CH3:27].C(N(CC)CC)C.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>[OH:15][C@@H:7]([CH2:8][C@@H:9]([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH2:11])[C@@H:6]([NH:5][C:3]([C@@H:2]([NH:1][C:42]([C@@H:34]([NH:33][C:31](=[O:32])[O:30][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:43])[CH2:20][C:21]1[N:22]=[CH:23][NH:24][CH:25]=1)=[O:4])[CH2:16][CH:17]([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178456024HCID 178456024, compound

Product 1

HCID 178456022HCID 178456022, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 880 mg (2.5 mmol) of (S)-α-amino-N-[(1S,2S,4S)-2-hydroxy-1-isobutyl-4-isopropyl-5-hexenyl]-imidazole-4-propionamide. 1.99 g (7.5 mmol) of t-butoxycarbonyl-L-phenylalanine. 1.05 ml (7.5 mmol) of triethylamine and 3.32 g (7.5 mmol) of BOP in 100 ml of acetonitrile was stirred at room temperature for 6 days. Thereafter, the solvent was evaporated and the residue was dissolved in ethyl acetate and washed in succession with 2N sodium bicarbonate solution, saturated ammonium chloride solution, again with 2N sodium bicarbonate solution and again with saturated ammonium chloride solution. The organic solution was dried over sodium sulfate and evaporated and the residue was triturated twice with hexane. The residue was chromatographed on 100 g of silica gel with a 98:2 mixture of chloroform and methanol. Recrystallization of the thus-obtained crude product from methylene chloride and hexane yielded 400 mg of t-butyl [(S)-α-[[(S)-1-[[(1S,2S,4S)-2-hydroxy-1-isobutyl-4 -isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate as a white powder, melting point 82°.

Workup

  1. customThereafter, the solvent was evaporated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed in succession with 2N sodium bicarbonate solution, saturated ammonium chloride solution, again with 2N sodium bicarbonate solution and again with saturated ammonium chloride solution
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. customevaporated
  6. customthe residue was triturated twice with hexane
  7. customThe residue was chromatographed on 100 g of silica gel with a 98:2 mixture of chloroform and methanol
  8. customRecrystallization of the
  9. customthus-obtained crude product from methylene chloride and hexane

Sources & evidence

ORD record
ord-c4ca8faa814942cfa3c9c0f24d2e18b6
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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