1,1'-Carbonyldiimidazole → HCID 54320728, compound

HRID 1156815Notes

Reaction equation

HRID 1156815 reaction equation
Cl.[CH:2]1([C@@H:8]2[CH2:12][NH:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C[Si]([CH:20]([Si](C)(C)C)[C:21]#N)(C)C.C(O[CH:30]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[CH2:31][CH2:32][CH2:33][PH:34]([CH2:36][C:37](O)=[O:38])=[O:35])C.C(N1C=CN=C1)(N1C=CN=C1)=[O:47]>C(#N)C>[CH:2]1([C@@H:8]2[CH2:12][N:11]([C:37](=[O:38])[CH2:36][P:34]([O:35][CH2:21][CH3:20])([CH2:33][CH2:32][CH2:31][CH2:30][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:47])[C@H:10]([C:13]([OH:15])=[O:14])[CH2:9]2)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 11008620HCID 11008620, compoundHCID 12805592HCID 12805592, compoundHCID 178467815HCID 178467815, compound

Product 1

HCID 54320728HCID 54320728, compoundYield 256%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

(cis)-4-Cyclohexyl-L-proline hydrochloride (3.0 g) in 30 ml acetonitrile is treated with bis(trimethylsilyl)acetonitrile (0.525 g) and stirred until the solid has dissolved. Meanwhile, [(ethoxy) (phenylbutyl)]phosphinyl acetic acid (4.0 g) and carbonyldiimidazole (3.87 g) in 70 ml of acetonitrile are stirred at 0° C. for one hour. The two solutions are combined and stirred for about 16 hours. The mixture is concentrated and the residue is taken up in dichloromethane, washed with 5% potassium bisulfate, and brine, dried (MgSO4) and evaporated to an oil which is chromatographed (20% acetic acid/benzene) to yield 3.36 g of the title compound.

Workup

  1. dissolutionhas dissolved
  2. stirringstirred for about 16 hours
  3. concentrationThe mixture is concentrated
  4. washwashed with 5% potassium bisulfate, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated to an oil which
  7. customis chromatographed (20% acetic acid/benzene)

Sources & evidence

ORD record
ord-60d094de1ee54223a1600adfcef4d3b3
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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