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 931671Notes

Reaction equation

HRID 931671 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-e233bd226822492b8431f7a420d620e1
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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