Sodium Bicarbonate → HCID 86663418, compound

HRID 446495Notes

Reaction equation

HRID 446495 reaction equation
C(=O)([O-])O.[Na+].[NH:6]1[CH2:11][CH2:10][C:9]2([C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C@@H:12]2[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:8][CH2:7]1.CS(O[CH2:32][CH2:33][C@:34]1([C:55]2[CH:60]=[CH:59][C:58]([F:61])=[CH:57][CH:56]=2)[O:38][CH2:37][N:36]([C:39](=[O:54])[C:40]2[CH:45]=[C:44]([C:46]([F:49])([F:48])[F:47])[CH:43]=[C:42]([C:50]([F:53])([F:52])[F:51])[CH:41]=2)[CH2:35]1)(=O)=O>C(#N)C>[F:52][C:50]([F:51])([F:53])[C:42]1[CH:41]=[C:40]([CH:45]=[C:44]([C:46]([F:49])([F:47])[F:48])[CH:43]=1)[C:39]([N:36]1[CH2:35][C@@:34]([CH2:33][CH2:32][N:6]2[CH2:11][CH2:10][C:9]3([C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][C@@H:12]3[O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:8][CH2:7]2)([C:55]2[CH:56]=[CH:57][C:58]([F:61])=[CH:59][CH:60]=2)[O:38][CH2:37]1)=[O:54]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 86663416HCID 86663416, compoundHCID 86663417HCID 86663417, compound

Product 1

HCID 86663418HCID 86663418, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium hydrogencarbonate (7.15 g, 85.11 mmol) was added to a solution of the crude product (32.1 g) obtained in Example 1h and the compound (37.6 g, 70.9 mmol) obtained in Example 1d in acetonitrile (160 mL) with stirring at room temperature, and the mixture was stirred at reflux temperature under a nitrogen atmosphere for 14 hours. The reaction mixture was left to stand for cooling to room temperature, and then the organic solvent was evaporated under reduced pressure. An aqueous sodium hydrogencarbonate solution was added to the resulting residue, and the mixture was extracted with ethyl acetate. The organic layers were combined and dried with anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1→0:1, v/v) to give the title compound (47.8 g; yield, 93%) as a white solid.

Workup

  1. temperatureat reflux temperature under a nitrogen atmosphere for 14 hours
  2. waitThe reaction mixture was left
  3. customthe organic solvent was evaporated under reduced pressure
  4. additionAn aqueous sodium hydrogencarbonate solution was added to the resulting residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=2:1→0:1, v/v)

Sources & evidence

ORD record
ord-26dba05cbc994838ac9fbd103eacc21f
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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