Sodium Bicarbonate → HCID 20675274, compound

HRID 244260Notes

Reaction equation

HRID 244260 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:18][C@@H:19]1[C@@:23]([CH2:43][O:44]S(C2C=CC(C)=CC=2)(=O)=O)([CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:22][C@@H:21]([N:55]2[CH:62]=[C:61]([CH3:63])[C:59](=[O:60])[NH:58][C:56]2=[O:57])[C@@H:20]1O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:11]([O:18][C@@H:19]1[C@@:23]2([CH2:43][O:44][C@H:20]1[C@H:21]([N:55]1[CH:62]=[C:61]([CH3:63])[C:59](=[O:60])[NH:58][C:56]1=[O:57])[O:22]2)[CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:40])[CH3:41])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 20675275HCID 20675275, compound

Product 1

HCID 20675274HCID 20675274, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, sodium bis(trimethylsilyl)amide (1.0 M in THF, 8.47 ml, 8.47 mmols) was added, under cooling with ice, to a tetrahydrofuran solution (30 ml) of Compound 36 (1.86 g, 2.42 mmols), and the mixture was stirred for 1 hour at room temperature. A saturated sodium bicarbonate solution (14 ml) was added to the reaction mixture, and then the solvent was distilled off under reduced pressure. After water was added to the residue, the mixture was extracted with chloroform. The organic phase was washed with a saturated sodium chloride solution, and then dried over sodium sulfate. The solvents were distilled off under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 2:3) to obtain a white powder, Compound 37 (1.42 g, 2.37 mmols, 98%).

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionAfter water was added to the residue
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic phase was washed with a saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. distillationThe solvents were distilled off under reduced pressure
  7. customthe resulting crude product was purified by silica gel column chromatography (AcOEt-hexane, 2:3)

Sources & evidence

ORD record
ord-eef8234cf6674c7f830748531f1014f4
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

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