1,1'-Carbonyldiimidazole → HCID 178475051, compound

HRID 1766604Notes

Reaction equation

HRID 1766604 reaction equation
[C:1]([NH:4][C@@H:5]1[C@@H:10]([NH:11]/[C:12](/[NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:13]\[C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=[C:8]([C:29]([O:31][CH:32]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[O:30])[O:7][C@H:6]1[C@H:45]([OH:50])[C@H:46]([OH:49])[CH2:47][OH:48])(=[O:3])[CH3:2].[C:51](N1C=CN=C1)(N1C=CN=C1)=[O:52]>C(#N)C>[C:1]([NH:4][C@@H:5]1[C@@H:10]([NH:11][C:12]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[N:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]=[C:8]([C:29]([O:31][CH:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)=[O:30])[O:7][C@H:6]1[C@H:45]([OH:50])[C@H:46]1[CH2:47][O:48][C:51](=[O:52])[O:49]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-Carbonyldiimidazole2×HCID 178475052HCID 178475052, compound

Product 1

HCID 178475051HCID 178475051, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Benzhydryl (2R,3R,4S)-3-(acetylamino)-4-({(E)-[(tert-butoxycarbonyl)amino][(tert-butoxycarbonyl)imino]methyl}amino)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylate (see J. Med. Chem. 1998, 41, 787–797) (12.38 g; 17.7 mmoles) was dissolved in dry acetonitrile (130 ml) under nitrogen at room temperature. The solution was stirred and 1,1′-carbonyldiimidazole (2.87 g; 17.7 mmoles) was added. After 16 hours LC/MS showed the presence of starting triol so further 1,1′-carbonyldiimidazole (total of 0.493 g; 3 mmoles) was added. After a few hours LC/MS showed no triol present. The solvent was evaporated and the residue flash columned on silica, eluting with 1:1 ethyl acetate/40–60 petroleum ether. Fractions containing wanted product were evaporated then taken up in dichloromethane, dried with sodium sulphate, filtered and evaporated to give Intermediate 1 as an off white solid (11.05 g; 86%).

Workup

  1. waitAfter a few hours LC/MS showed
  2. customThe solvent was evaporated
  3. washeluting with 1:1 ethyl acetate/40–60 petroleum ether
  4. additionFractions containing
  5. customwere evaporated
  6. dry with materialdried with sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-ba8221eb226d4eb4a9c39d0fb538de3e
Source dataset
uspto-grants-2007_06
Patent number
US07230114B2

Reaction notes

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