Diisopropylethylamine → HCID 178456005, compound

HRID 1655733Notes

Reaction equation

HRID 1655733 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].CCN(C(C)C)C(C)C.[CH3:38][C:39]([CH3:56])([CH3:55])[CH2:40][C:41]([O:43][C@@H:44]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:45](O)=[O:46])=[O:42].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(=O)(O)[O-].[Na+]>C(#N)C>[CH3:38][C:39]([CH3:56])([CH3:55])[CH2:40][C:41]([O:43][C@H:44]([C:45](=[O:46])[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][C@@H: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)[CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)=[O:42]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 54316995(S)-alpha-[(3,3-dimethylbutyryl)oxy]hydrocinnamic acidHCID 178456019HCID 178456019, compound

Product 1

HCID 178456005HCID 178456005, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

90 mg (0.23 mmol) of (S)-α-amino-N- [(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide and 0.047 ml of Hunig base in 2ml of acetonitrile were treated dropwise at room temperature with a solution of 60.7 mg of (S)-α-[(3,3-dimethylbutyryl)oxy]hydrocinnamic acid and 101 mg of BOP in 5 ml of acetonitrile. The mixture was stirred at room temperature for 4 hours, subsequently poured into 2N sodium bicarbonate solution and extracted with methylene chloride. The organic phase was washed with ammonium chloride solution and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel. After elution with a 20:1 mixture of methylene chloride and methanol, there were obtained 50 mg (34%) of (S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl 5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl 3,3-dimethylbutyrate as a yellow oil. MS: 637 (M+H)+.

Workup

  1. extractionextracted with methylene chloride
  2. washThe organic phase was washed with ammonium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was chromatographed on silica gel
  6. washAfter elution
  7. additionwith a 20:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-623335428ed34dafb2f0dd4be177c02d
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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