Diisopropylethylamine → HCID 178448277, compound

HRID 847307Notes

Reaction equation

HRID 847307 reaction equation
[NH2:1][C@H:2]([C@@H:10]([OH:25])[CH2:11][C@@H:12]([CH:22]([CH3:24])[CH3:23])[CH2:13][CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:3][CH:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1.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.[NH:62]([C:84]([O:86][C:87]([CH3:90])([CH3:89])[CH3:88])=[O:85])[C@H:63]([C:71]([NH:73][C@H:74]([C:81](O)=[O:82])[CH2:75][C:76]1[N:80]=[CH:79][NH:78][CH:77]=1)=[O:72])[CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>C(#N)C.C(OCC)(=O)C>[CH:4]1([CH2:3][C@H:2]([NH:1][C:81]([CH:74]([NH:73][C:71]([C@@H:63]([NH:62][C:84](=[O:85])[O:86][C:87]([CH3:89])([CH3:88])[CH3:90])[CH2:64][C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)=[O:72])[CH2:75][C:76]2[N:80]=[CH:79][NH:78][CH:77]=2)=[O:82])[C@@H:10]([OH:25])[CH2:11][C@@H:12]([CH:22]([CH3:23])[CH3:24])[CH2:13][CH2:14][O:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 22845418HCID 22845418, compoundHCID 178454152HCID 178454152, compound

Product 1

HCID 178448277HCID 178448277, compoundYield 61.8%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

174 mg (0.5 mmol) of (2S,3S,5S)-2-amino-1-cyclohexyl-5-isopropyl-7-phenoxy-3-heptanol are dissolved in 8 ml of acetonitrile, the solution is treated with 0.102 ml (0.5 mmol) of Hunig base, 220 mg (0.5 mmol) of BOP and 204 mg (0.5 mmol) of Boc-Phe-His-OH and the reaction mixture is stirred at room temperature for 3.5 hours. Thereafter, the mixture is taken up in ethyl acetate and the organic phase is washed once each time with 1N hydrochloric acid and 2N sodium carbonate solution, dried over sodium sulphate and evaporated under reduced pressure. Chromatography of the residue on silica gel with a 15:1 mixture of methylene chloride and methanol as the eluting agent yields 226 mg (60%) of t-butyl [(S)-α-[[1-[[(1S,2S,4S)-1-(cyclohexylmethyl)-2-hydroxy-4-isopropyl-6-phenoxyhexyl]carbamoyl]-2-imidazol-4-ylethyl]carbamoyl]phenethyl]carbamate as a resin, MS: 732 (M+ H)+.

Workup

  1. washthe organic phase is washed once each time with 1N hydrochloric acid and 2N sodium carbonate solution
  2. dry with materialdried over sodium sulphate
  3. customevaporated under reduced pressure
  4. additionChromatography of the residue on silica gel with a 15:1 mixture of methylene chloride and methanol as the eluting agent

Sources & evidence

ORD record
ord-398017ddd77d4294b79b8b3818935403
Source dataset
uspto-grants-1992_08
Patent number
US05140011

Reaction notes

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