Diisopropylethylamine → HCID 178446064, compound

HRID 1655735Notes

Reaction equation

HRID 1655735 reaction equation
[NH2:1][C@@H:2]([CH2:23][C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)[C:3]([NH:5][C@@H:6]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C@@H:7]([OH:15])[CH2:8][C@@H:9]([CH:12]([CH3:14])[CH3:13])[CH:10]=[CH2:11])=[O:4].[CH3:29]CN(C(C)C)C(C)C.[C:38]1([CH:44]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:45]([O:47][C@@H:48]([CH2:52][C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[C:49]([OH:51])=O)=[O:46])C=CC=CC=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:76]2[CH:77]=[CH:78][CH:79]=[CH:80][C:75]=2N=N1>C(#N)C>[CH2:38]([CH:44]([CH2:59][C:64]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:29]=1)[C:45]([O:47][C@H:48]([C:49](=[O:51])[NH:1][C@H:2]([C:3](=[O:4])[NH:5][C@@H:6]([CH2:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1)[C@@H:7]([OH:15])[CH2:8][CH:9]([CH:12]([CH3:13])[CH3:14])[CH:10]=[CH2:11])[CH2:23][C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)[CH2:52][C:53]1[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=1)=[O:46])[C:75]1[CH:80]=[CH:79][CH:78]=[CH:77][CH:76]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 54325350(S)-alpha-(diphenylacetoxy)hydrocinnamic acidHCID 178456019HCID 178456019, compound

Product 1

HCID 178446064HCID 178446064, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

100 mg (0.256 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide and 0.052 ml of Hunig base in 2 ml of acetonitrile were treated with 92 mg of (S)-α-(diphenylacetoxy)hydrocinnamic acid and 113 mg of BOP in 2 ml of acetonitrile and stirred at room temperature for 12 hours. The reaction solution was then poured onto 1N hydrochloric acid/ice, extracted with ethyl acetate, the organic phase was washed with sodium carbonate solution, dried over sodium sulfate and, finally, the solvent was removed under reduced pressure. The residue was chromatographed on silica gel with a 10:1 mixture of methylene chloride and methanol, to obtain 130 mg of (S)-α-[[(S)-1-[[(1S,2S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl dibenzylacetate in the form of an amorphous solid. MS 733 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe organic phase was washed with sodium carbonate solution
  3. dry with materialdried over sodium sulfate
  4. customfinally, the solvent was removed under reduced pressure
  5. customThe residue was chromatographed on silica gel with a 10:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-15269954eb814dc49f2d0c078e5135f2
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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