Triethylamine → (3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonate

HRID 931681Notes

Reaction equation

HRID 931681 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]([O:9][C@@H:10]1[C@@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:36]([O:42][C:43](=[O:45])[CH3:44])[C@@H:35]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[O:34][C@H:11]1[O:12][C:13]1[C:17]([CH2:18][C:19]2[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][CH2:28][OH:29])=[CH:21][C:20]=2[CH3:30])=[C:16]([CH:31]([CH3:33])[CH3:32])[NH:15][N:14]=1)(=[O:8])[CH3:7].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:29][CH2:28][CH2:27]/[CH:26]=[CH:25]/[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][C:17]2[C:13]([O:12][C@@H:11]3[O:34][C@H:35]([CH2:46][O:47][C:48](=[O:50])[CH3:49])[C@@H:36]([O:42][C:43](=[O:45])[CH3:44])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:10]3[O:9][C:6](=[O:8])[CH3:7])=[N:14][NH:15][C:16]=2[CH:31]([CH3:33])[CH3:32])=[C:20]([CH3:30])[CH:21]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 867151534-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside

Product 1

HCID 86701862(3E)-4-[3-methyl-4-({5-(propan-2-yl)-3-[(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)oxy]-1H-pyrazol-4-yl}methyl)phenyl]but-3-en-1-yl methanesulfonateYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add methanesulfonyl chloride (0.54 mL, 7 mmol) to a solution of 4-{4-[(1E)-4-hydroxybut-1-en-1-yl]-2-methylbenzyl}-5-(propan-2-yl)-1H-pyrazol-3-yl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside (3.7, 5.87 mmol) in dichloromethane (15 mL) and triethylamine (4 mL, 29 mmol) at 0° C. After refluxing at room temperature for 30 min, concentrate to remove the solvent under the reduced pressure. Purify residue by flash chromatography to yield the title compound (2.9 g, 4.1 mmol).

Workup

  1. concentrationconcentrate
  2. customto remove the solvent under the reduced pressure

Sources & evidence

ORD record
ord-1b19cbfe2813427f8f33f14cb2b76058
Source dataset
uspto-grants-2016_03
Patent number
US09296775B2

Reaction notes

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