Sodium Bicarbonate → HCID 136344205, compound

HRID 244266Notes

Reaction equation

HRID 244266 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH2:11]([O:18][C@@H:19]1[C@@:23]([CH2:43]OS(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[C:70]3[N:69]=[C:62]([NH:63][C:64](=[O:68])[CH:65]([CH3:67])[CH3:66])[NH:61][C:59](=[O:60])[C:58]=3[N:57]=[CH:56]2)[C@@H:20]1[OH:71])[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:71][C@H:20]1[C@H:21]([N:55]1[C:70]3[N:69]=[C:62]([NH:63][C:64](=[O:68])[CH:65]([CH3:67])[CH3:66])[NH:61][C:59](=[O:60])[C:58]=3[N:57]=[CH:56]1)[O:22]2)[CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:40])[CH3:41])([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=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 136393286HCID 136393286, compound

Product 1

HCID 136344205HCID 136344205, compoundYield 156.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, sodium bis(trimethylsilyl)amide (1.0 M in THF, 0.31 ml, 0.315 mmol) was added to a tetrahydrofuran solution (3.0 ml) of Compound 45 (92.1 mg, 0.102 mmol) at room temperature, and the mixture was stirred for 3 hours at room temperature. A saturated sodium bicarbonate solution was added to the reaction mixture, and then the system was extracted 3 times with methylene chloride. 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 (CHCl3-MeOH, 25:1) to obtain a white powder, Compound 46 (31.4 mg, 0.160 mmol, 44%).

Workup

  1. extractionthe system was extracted 3 times with methylene chloride
  2. washThe organic phase was washed with a saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. distillationThe solvents were distilled off under reduced pressure
  5. customthe resulting crude product was purified by silica gel column chromatography (CHCl3-MeOH, 25:1)

Sources & evidence

ORD record
ord-2fb4299af5da43a1bd9eb26df0d7219a
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

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