Diisopropylethylamine → HCID 178513886, compound

HRID 1655739Notes

Reaction equation

HRID 1655739 reaction equation
N[C@@H:2]([CH2:23][C:24]1[N:25]=[CH:26][NH:27][CH:28]=1)[C:3]([NH:5][C@@H](CC1CCCCC1)[C@@H](O)C[C@@H](C(C)C)C=C)=[O:4].CCN(C(C)C)C(C)C.O1CCN(NC(N[C@H](C(O)=O)CC2C=CC=CC=2)=O)CC1.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>[NH:27]1[CH:28]=[C:24]([CH2:23][CH2:2][C:3]([NH2:5])=[O:4])[N:25]=[CH:26]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 54167396N-(morpholinocarbamoyl)-3-phenyl-L-alanineHCID 178456019HCID 178456019, compound

Product 1

HCID 178513886HCID 178513886, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

100 mg (0.52 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 at room temperature with 99 mg of N-(morpholinocarbamoyl)-3-phenyl-L-alanine and 113 mg of BOP in 2 ml of acetonitrile and stirred at room temperature for 12 hours. Thereafter, the reaction solution was poured onto 1N hydrochloric acid/ice, extracted with ethyl acetate, the organic extracts were dried over sodium sulfate and the solvent was removed under reduced pressure. The residue was chromatoqraphed on silica gel with a 10:1 mixture of methylene chloride and methanol, to obtain 130 mg (67%) of (S)-N-[(1S,2S,4S)-1-(cyclohexyl-methyl)-2-hydroxy-4-isopropyl-5 hexenyl]-α-2-[N-(morpholinocarbamoyl)-3-phenyl-L-alanyl]amino]imidazole-4-propionamide as an amorphous solid. MS: 651 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic extracts were dried over sodium sulfate
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was chromatoqraphed on silica gel with a 10:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-ec360e3ff1b444649f98fd379a247f5d
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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