Diisopropylethylamine → HCID 178456003, compound

HRID 1655741Notes

Reaction equation

HRID 1655741 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([O:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C@H:14]([C:22](O)=[O:23])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:12])=[CH:3][CH:2]=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.[NH2:58][C@@H:59]([CH2:80][C:81]1[N:82]=[CH:83][NH:84][CH:85]=1)[C:60]([NH:62][C@@H:63]([CH2:73][CH:74]1[CH2:79][CH2:78][CH2:77][CH2:76][CH2:75]1)[C@@H:64]([OH:72])[CH2:65][C@@H:66]([CH:69]([CH3:71])[CH3:70])[CH:67]=[CH2:68])=[O:61].CCN(C(C)C)C(C)C>C(#N)C>[C:1]1([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:2]=[CH:3][C:4]([O:7][CH2:8][CH2:9][NH:10][C:11]([NH:13][C@H:14]([C:22](=[O:23])[NH:58][C@H:59]([C:60](=[O:61])[NH:62][C@@H:63]([CH2:73][CH:74]2[CH2:75][CH2:76][CH2:77][CH2:78][CH2:79]2)[C@@H:64]([OH:72])[CH2:65][C@@H:66]([CH:69]([CH3:70])[CH3:71])[CH:67]=[CH2:68])[CH2:80][C:81]2[N:82]=[CH:83][NH:84][CH:85]=2)[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:12])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22847743HCID 22847743, compoundHCID 178456019HCID 178456019, compound

Product 1

HCID 178456003HCID 178456003, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 103 mg of N-[[2-(4-biphenyloxy)ethyl ]carbamoyl]-3-phenyl-L-alanine and 113 mg of BOP in acetonitrile was added to 100 mg (0.256 mmol) of (S)-α-amino-N-[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]imidazole-4-propionamide 0.052 ml of Hunig base in 5 ml of acetonitrile, and the mixture was subsequently stirred at room temperature for 12 hours. Subsequently the reaction mixture was poured onto 1N hydrochloric acid/ice, extracted with ethyl acetate, the extracts were dried over sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by chromatography on silica gel with a 10:1 mixture of methylene chloride and methanol, to obtain 90 mg (45%) of 1-[2-(4-biphenyloxy)ethyl]-3-[(S)-α-[[(S)-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-5-hexenyl]carbamoyl]-2-imidazol-4-ylethyl]- carbamoyl]phenethyl]urea as an amorphous powder. MS: 777 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe extracts were dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure
  4. customThe crude product was purified by chromatography on silica gel with a 10:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-91d43aee2cce49b0b896f76d96584cf5
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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