Dichloromethane → 4-(4-bromo-2-methylbenzyl)-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranoside

HRID 2366515Notes

Reaction equation

HRID 2366515 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([OH:17])=[N:11][NH:12][C:13]=2[CH:14]([CH3:16])[CH3:15])=[C:4]([CH3:18])[CH:3]=1.[C:19]([OH:27])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:28]([OH:36])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[C:37]([OH:45])(=[O:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.[C:46]([OH:54])(=[O:53])[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[C@H:55]1(Br)[O:63][C@H:62]([CH2:64]O)[C@@H:60](O)[C@H:58](O)[C@H:56]1O.ClCCl.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O>[C:19]([O:27][C@@H:56]1[C@@H:58]([O:35][C:28](=[O:36])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C@H:60]([O:44][C:37](=[O:45])[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C@@H:62]([CH2:64][O:53][C:46](=[O:54])[C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[O:63][C@H:55]1[O:17][C:10]1[C:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][C:4]=2[CH3:18])=[C:13]([CH:14]([CH3:15])[CH3:16])[NH:12][N:11]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 86720879benzoic acid;(2R,3R,4S,5S,6R)-2-bromo-6-(hydroxymethyl)oxane-3,4,5-triolHCID 178422431HCID 178422431, compound

Product 1

HCID 867208784-(4-bromo-2-methylbenzyl)-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-benzoyl-beta-D-glucopyranosideYield 98.9%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolvent

Procedure

To a 1 L flask, add 4-[(4-bromo-2-methyl-phenyl)methyl]-5-isopropyl-1H-pyrazol-3-ol (20 g, 64.7 mmol), alpha-D-glucopyranosyl bromide tetrabenzoate (50 g, 76 mmol), benzyltributylammonium chloride (6 g, 19.4 mmol), dichloromethane (500 mL), potassium carbonate (44.7 g, 323 mmol) and water (100 mL). Stir the reaction mixture overnight at room temperature. Extract with dichloromethane (500 mL). Wash extract with water (300 mL) and brine (500 mL). Dry organic phase over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by flash chromatography to yield the title compound (37 g, 64 mmol). MS (m/z): 889.2 (M+1), 887.2 (M−1).

Workup

  1. extractionExtract with dichloromethane (500 mL)
  2. washWash
  3. extractionextract with water (300 mL) and brine (500 mL)
  4. filtrationDry organic phase over sodium sulfate, filter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the residue by flash chromatography

Sources & evidence

ORD record
ord-b4acc912d8e9454f9ab63e9f48f30bbf
Source dataset
uspto-grants-2014_04
Patent number
US08697849B2

Reaction notes

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