Sodium Bicarbonate → HCID 70010871, compound

HRID 1250794Notes

Reaction equation

HRID 1250794 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 stilted 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 (6H, multiplets, 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-3a84149ad7bb4ff69ebea112db3e802e
Source dataset
uspto-grants-2002_01
Patent number
US06339147B1

Reaction notes

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