Diisopropylethylamine → HCID 178456002, compound

HRID 1655737Notes

Reaction equation

HRID 1655737 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.[CH2:38]([N:45]([CH2:60][C:61]1[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=1)[C:46]([NH:48][C@H:49]([C:57](O)=[O:58])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=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>[CH2:60]([N:45]([CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:46]([NH:48][C@H:49]([C:57](=[O:58])[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)[CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)=[O:47])[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 53649524HCID 53649524, compoundHCID 178456019HCID 178456019, compound

Product 1

HCID 178456002HCID 178456002, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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 at room temperature with 100 mg of N-(dibenzylcarbamoyl)-3-phenyl-L-alanine and 113 mg of BOP and subsequently stirred at room temperature for 12 hours. Thereafter, the reaction solution was poured onto 1N hydrochloric acid/ice, extracted with ethyl acetate, the extracts were dried over sodium sulfate and the solvent was removed under reduced pressure. Chromatography of the residue on silica gel using a 10:1 mixture of methylene chloride and methanol as the eluting agent yielded 130 mg of 1,1-dibenzyl-3-[(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]urea in the form of an amorphous solid. MS: 761 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-b252782c8a7f49fcad0c2e6d69760bef
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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