Methanol → HCID 178471574, compound

HRID 2226021Notes

Reaction equation

HRID 2226021 reaction equation
O1CCCCC1[O:7][CH2:8][CH:9]([C:28]1[CH:49]=[CH:48][C:31]([C:32]([NH:34][C@H:35]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:33])=[CH:30][CH:29]=1)[CH2:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])[N:20]=[C:14]2[N:13]=[CH:12]1.C(=O)([O-])[O-].[Na+].[Na+].CO>Cl.O>[OH:7][CH2:8][CH:9]([C:28]1[CH:29]=[CH:30][C:31]([C:32]([NH:34][C@H:35]([C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[O:33])=[CH:48][CH:49]=1)[CH2:10][N:11]1[C:16]([OH:17])=[C:15]2[CH:18]=[C:19]([NH:21][C:22](=[O:27])[C:23]([CH3:24])([CH3:25])[CH3:26])[N:20]=[C:14]2[N:13]=[CH:12]1

Participants

6

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 178418637HCID 178418637, compound

Product 1

HCID 178471574HCID 178471574, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

The solution of 0.94 g of diethyl N-[4-(1-(tetrahydropyr-2-yloxy)-3-(4-hydroxy-6-pivaloylaminopyrrolo-[2,3-d]pyrimidin-3-yl)prop-2-yl)benzoyl]glutamate in 40 ml of 0.1N methanolic hydrogen chloride is stirred at ambient temperatures for 2 hours. The reaction mixture is neutralized with a solution of 205 mg of sodium carbonate in 10 ml of water and most of methanol removed by evaporation under reduced pressure. One hundred milliliters of methylene chloride are added and the solution is washed twice with 20 ml of water, dried over anhydrous magnesium sulfate, and concentrated. The residue is triturated with 1:2 ethyl acetate and ether, filtered, and dried to give diethyl N-[4-{1-hydroxy-3-(4-hydroxy-6-pivaloylaminopyrrolo[2,3-d]-pyrimidin-3-yl)prop-2-yl}benzoyl]glutamate.

Workup

  1. customremoved by evaporation under reduced pressure
  2. additionOne hundred milliliters of methylene chloride are added
  3. washthe solution is washed twice with 20 ml of water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is triturated with 1:2 ethyl acetate and ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-1033682d345e4ebdbaf2244e908cef56
Source dataset
uspto-grants-1994_09
Patent number
US05344932

Reaction notes

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