Sodium Carbonate → HCID 9961317, compound

HRID 1168274Notes

Reaction equation

HRID 1168274 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([C:14]2[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=2)[O:7][C@H:6]1[N:21]1[CH:29]=[N:28][C:27]2[C:22]1=[N:23][C:24]([CH2:45][NH:46][S:47]([CH2:50][CH:51]([CH3:53])[CH3:52])(=[O:49])=[O:48])=[N:25][C:26]=2[NH:30][CH2:31][CH:32]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>CO.O>[C:39]1([CH:32]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:31][NH:30][C:26]2[N:25]=[C:24]([CH2:45][NH:46][S:47]([CH2:50][CH:51]([CH3:52])[CH3:53])(=[O:48])=[O:49])[N:23]=[C:22]3[C:27]=2[N:28]=[CH:29][N:21]3[C@H:6]2[C@H:5]([OH:4])[C@H:9]([OH:10])[C@@H:8]([C:14]3[N:15]=[N:16][N:17]([CH2:19][CH3:20])[N:18]=3)[O:7]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 70024743HCID 70024743, compound

Product 1

HCID 9961317HCID 9961317, compoundYield 92.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (2R,3R,4R,5R)-4-(acetyloxy)-2-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulphonyl)amino]methyl}-9H-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 26) (230 mg, 0.31 mmol) and sodium carbonate (130 mg, 1.23 mmol) in methanol (15 ml) and water (1.5 ml) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was partioned between ethyl acetate (50 ml) and water (10 ml). The organic layer was washed with brine (10 ml), dried (anhydrous sodium sulphate) and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (97:3 by volume). Product containing fractions were evaporated to afford the title compound as a white powder (190 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. washThe organic layer was washed with brine (10 ml)
  3. dry with materialdried (anhydrous sodium sulphate)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane:methanol (97:3 by volume)
  6. additionProduct containing fractions
  7. customwere evaporated

Sources & evidence

ORD record
ord-c39fae5d2b244b31a7d70aea5747d520
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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