Triethylamine → HCID 86602741, compound

HRID 2221426Notes

Reaction equation

HRID 2221426 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C@H:8]([OH:21])[CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[C:4]([O:24][C:25](=[O:27])[CH3:26])[CH:3]=1.C(N(CC)CC)C.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>C(OCC)(=O)C>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][CH2:7][C@H:8]([O:21][S:36]([CH3:35])(=[O:38])=[O:37])[CH2:9][N:10]2[C:14](=[O:15])[C:13]3=[CH:16][CH:17]=[CH:18][CH:19]=[C:12]3[C:11]2=[O:20])=[C:4]([O:24][C:25](=[O:27])[CH3:26])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69139366HCID 69139366, compound

Product 1

HCID 86602741HCID 86602741, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a reaction vessel were added crude (R)-1-(4-chloro-2-acetoxyphenoxy)-3-phthalimido-2-propanol 364 mg (0.90 mmol), triethylamine 137 mg (1.36 mmol) and ethyl acetate 2 mL. To this mixture was slowly dropped methanesulfonyl chloride 134 mg (1.18 mmol) in an ice bath and then the mixture was stirred at room temperature for 3 hours. After washing with an aqueous 5% HCl solution and water successively, the organic layer was taken and the solvent was evaporated to give crude (R)-1-(4-chloro-2-acetoxyphenoxy)-2-methanesulfonyloxy-3-phthalimidopropane 213 mg (yield 98%, chemical purity 97%) as a brown solid.

Workup

  1. washAfter washing with an aqueous 5% HCl solution and water successively
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-574d7a1713764bf1bd6da997304b1f97
Source dataset
uspto-grants-2008_05
Patent number
US07368608B2

Reaction notes

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