Diisopropylethylamine → HCID 67876623, compound

HRID 1655736Notes

Reaction equation

HRID 1655736 reaction equation
[NH2:1][C@@H:2]([CH2:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C@H:3]([CH2:5][C@@H:6]([CH:9]([CH3:11])[CH3:10])[CH:7]=[CH2:8])[OH:4].CCN(C(C)C)C(C)C.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:55]([CH2:58][C@H:59]([O:63][C:64](=[O:80])[CH:65]([CH2:73][C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)[CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:60](O)=[O:61])(=[O:57])[NH2:56]>C(#N)C>[CH2:73]([CH:65]([CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[C:64]([O:63][C@H:59]([C:60](=[O:61])[NH:1][C@@H:2]([CH2:12][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)[C@@H:3]([OH:4])[CH2:5][C@@H:6]([CH:9]([CH3:11])[CH3:10])[CH:7]=[CH2:8])[CH2:58][C:55](=[O:57])[NH2:56])=[O:80])[C:74]1[CH:75]=[CH:76][CH:77]=[CH:78][CH:79]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22847767HCID 22847767, compoundHCID 54059668HCID 54059668, compound

Product 1

HCID 67876623HCID 67876623, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 mg of (αS,βS)-β-amino-α-[(S)-2-isopropyl-3-butenyl]cyclohexanepropanol in 20 ml of acetonitrile were treated with 0.080 ml of Hunig base, 174 mg of BOP and 140 mg of (S)-3-carbamoyl-2-(dibenzylacetoxy)propionic acid and 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 washed with sodium carbonate solution and, finally, dried over sodium sulfate. The solvent was then removed under reduced pressure and the residue was chromatographed on silica gel with a 20:1 mixture of methylene chloride and methanol, to obtain 142 mg (60%) of (S)-2-carbamoyl-1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2 -hydroxy-4-isopropyl-5-hexenyl]- carbamoyl]ethyl dibenzylacetate in the form of a resin. MS: 591 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extracts were washed with sodium carbonate solution
  3. dry with materialfinally, dried over sodium sulfate
  4. customThe solvent was then removed under reduced pressure
  5. customthe residue was chromatographed on silica gel with a 20:1 mixture of methylene chloride and methanol

Sources & evidence

ORD record
ord-759b477149b74ac7b2acc32f70fa7cfc
Source dataset
uspto-grants-1993_10
Patent number
US05250517

Reaction notes

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