Sodium Bicarbonate → HCID 70010871, compound

HRID 1266639Notes

Reaction equation

HRID 1266639 reaction equation
CO[C:3]1[C:4](OC)=[C:5]([CH:20]=[CH:21][CH:22]=1)[C:6](Cl)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:25]([O:28][CH:29]([O:45][C:46](=[O:48])[CH3:47])[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]([OH:44])[CH2:42][OH:43])=[CH:32][CH:31]=1)(=[O:27])[CH3:26].[C:49](=[O:52])(O)[O-].[Na+].[C:54](OCC)(=[O:56])C.CCCCCC>N1C=CC=CC=1>[C:46]([O:45][CH:29]([O:28][C:25](=[O:27])[CH3:26])[C:30]1[CH:31]=[CH:32][C:33]([O:36][CH2:37][CH2:38][CH2:39][CH2:40][CH:41]([OH:44])[CH2:42][O:43][C:6]([C:13]2[CH:14]=[CH:15][C:16]([O:52][CH3:49])=[CH:17][CH:18]=2)([C:5]2[CH:4]=[CH:3][C:22]([O:56][CH3:54])=[CH:21][CH:20]=2)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:34][CH:35]=1)(=[O:48])[CH3:47]

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 21226206Ethyl acetate hexaneHCID 22966850HCID 22966850, compoundHCID 66624882Dimethoxytrityl chloride

Product 1

HCID 70010871HCID 70010871, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Dimethoxytrityl chloride (1.21 g, 3.57 mmol) was added to a solution of 8 (1.0 g, 2.94 mmol) in 17 ml of dry pyridine. The solution was stirred at room temperature for 2 h. and then poured into 250 ml of 5% sodium bicarbonate and extracted with 300 ml of ethyl acetate. The extract was dried over sodium sulfate and evaporated. The residue was purified by silica gel chromatography eluting with 50% hexane in ethyl acetate (1% triethylamine). The pure product fractions were pooled and evaporated affording a foam: 1.66 g (85%) yield; TLC (1:1, ethyl acetate/hexane), Rf=0.50; 1H NMR (CDCl3) 7.62 (1H, s, acetal CH), 7.43 (2H, d, J=8.2 Hz, aromatic), 7.33-6.81 (17H, aromatic), 3.92 (2H, t, J=6.4 Hz, CH2), 3.78 (6H, s, OCH3), 3.17 (1H, dd, J=3.3 and 9.4 Hz, CH), 3.03 (1H, t, J=7.7 Hz, CH), 2.37 (1H, m, CH), 2.10 (6H, s, acetyl), 1.81-1.38 (6multiplets, CH2). Anal. Calcd for C38H42O9: C, 71.01; H, 6.59. Found: C, 70.91; H, 6.42.

Workup

  1. extractionextracted with 300 ml of ethyl acetate
  2. dry with materialThe extract was dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with 50% hexane in ethyl acetate (1% triethylamine)
  6. customevaporated
  7. customaffording a foam
  8. custom1.66 g (85%) yield

Sources & evidence

ORD record
ord-4ccd9e742752418fbf0c047b3caa9d55
Source dataset
uspto-grants-2003_04
Patent number
US06548652B2

Reaction notes

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