Triethylamine → HCID 178471407, compound

HRID 849735Notes

Reaction equation

HRID 849735 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]([CH2:13][PH:14]([CH2:16][OH:17])=[O:15])([O:10][CH2:11][CH3:12])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2].[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:18])[C:5]([CH2:13][PH:14]([CH2:16][O:17][S:20]([CH3:19])(=[O:22])=[O:21])=[O:15])([O:10][CH2:11][CH3:12])[CH2:6][CH:7]([CH3:9])[CH3:8])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178471406HCID 178471406, compound

Product 1

HCID 178471407HCID 178471407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

2-(Ethoxy)(hydroxymethyl)phosphinoylmethyl-4-methylpentanoic acid ethyl ester (5 g) was dissolved in 20 mL of CH2Cl2 and cooled to -20° C. (in duplicate). Methanesulfonyl chloride (1.5 mL) and triethylamine (3.0 mL) were added to solution dropwise. After 15 minutes the bath was removed and the reaction left at room temperature for 31/2 hours. Each solution was then washed with 10 mL cold 2% HCl, 10 mL NaHCO3 (sat), 10 mL brine, dried with MgSO4, filtered and evaporated to yield 12.8 g (combined yield) of 2-(ethoxy)(methane-sulfonyloxymethyl)phosphinoylmethyl-4-methylpentanoic acid ethyl ester.

Workup

  1. customAfter 15 minutes the bath was removed
  2. washEach solution was then washed with 10 mL cold 2% HCl, 10 mL NaHCO3 (sat), 10 mL brine
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1c034951df924ddd83fce5784f83ddf9
Source dataset
uspto-grants-2000_01
Patent number
US06013792

Reaction notes

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