Sodium Bicarbonate → HCID 57794212, compound

HRID 2099984Notes

Reaction equation

HRID 2099984 reaction equation
Cl.C(OCC)C.[N+:7]([C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:21](=[O:22])[C:20]3[C:23]([CH2:38][N:39]([CH2:41][CH2:42][O:43][CH3:44])[CH3:40])=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:35][CH2:36][CH3:37])=[O:34])=[CH:28][CH:27]=4)[S:25][C:19]=3[N:18]([CH2:45][C:46]3[C:51]([F:52])=[CH:50][CH:49]=[CH:48][C:47]=3[F:53])[C:17]2=[O:54])=[CH:12][CH:11]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(O)C.[Pd]>[NH2:7][C:10]1[CH:11]=[CH:12][C:13]([N:16]2[C:21](=[O:22])[C:20]3[C:23]([CH2:38][N:39]([CH2:41][CH2:42][O:43][CH3:44])[CH3:40])=[C:24]([C:26]4[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:35][CH2:36][CH3:37])=[O:34])=[CH:28][CH:27]=4)[S:25][C:19]=3[N:18]([CH2:45][C:46]3[C:51]([F:52])=[CH:50][CH:49]=[CH:48][C:47]=3[F:53])[C:17]2=[O:54])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 10953452Ether hydrochlorideHCID 57794304HCID 57794304, compound

Product 1

HCID 57794212HCID 57794212, compoundYield 83.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2 N-hydrochloride/diethyl ether solution (20 ml) and 50% hydrous-10% palladium/carbon (1.00 g) were added to a solution of the compound of Example 96 (1.00 g) in ethanol (200 ml) and the mixture was stirred thoroughly under hydrogen atmosphere for 1 hour. The filtrate except a catalyst was neutralized with aqueous sodium bicarbonate, and then the solvent was distilled off. The obtained residue was partitioned between ethyl acetate and water, and then the organic layer was washed with saturated brine and dried over anhydride magnesium sulfate. The residue obtained by distilling off the solvent under the reduced pressure, was subject to NH-silica gel (manufactured by Fuji Silysia Chemical Ltd.) chromatography, and was recrystallized from methanol to give the title compound (0.80 g, 62%).

Workup

  1. distillationthe solvent was distilled off
  2. customThe obtained residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydride magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under the reduced pressure
  7. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-736bb844ac404fe9846291a2dc3d401f
Source dataset
uspto-grants-2009_08
Patent number
US07569570B2

Reaction notes

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