Sodium Bicarbonate → HCID 67132300, compound

HRID 244263Notes

Reaction equation

HRID 244263 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[C:72]3[N:71]=[CH:70][N:69]=[C:59]([NH:60][C:61](=O)[C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)[C:58]=3[N:57]=[CH:56]2)[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[C:72]3[N:71]=[CH:70][N:69]=[C:59]([NH:60][CH2:61][C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)[C:58]=3[N:57]=[CH:56]1)[O:22]2)[CH2:24][O:25][Si:26]([C:39]([CH3:42])([CH3:41])[CH3:40])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 54202017HCID 54202017, compound

Product 1

HCID 67132300HCID 67132300, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a stream of nitrogen, sodium bis(trimethylsilyl)amide (1.0 M in THF, 0.58 ml, 0.572 mmol) was added to a tetrahydrofuran solution (8.0 ml) of Compound 41 (210.5 mg, 0.238 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, 30:1) to obtain a white powder, Compound 42 (169.5 mg, 0.238 mmol, quant.).

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, 30:1)

Sources & evidence

ORD record
ord-71776ca1596b40ffb9f845b2dce79183
Source dataset
uspto-grants-2014_02
Patent number
USRE044779E1

Reaction notes

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