Triethylamine → HCID 22346420, compound

HRID 897339Notes

Reaction equation

HRID 897339 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl[CH2:18][CH2:19][S:20](Cl)(=[O:22])=[O:21]>ClCCl>[CH:19]([S:20]([NH:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])(=[O:22])=[O:21])=[CH2:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 151417Glycine tert-butyl ester

Product 1

HCID 22346420HCID 22346420, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cold (−10° C.) stirred solution of glycine tert-butyl ester (3.0 g, 22.9 mmol) and triethylamine (7.1 mL, 50.9 mmol) in dichloromethane (150 mL), 2-chloro-ethanesulfonyl chloride (2.4 m/L, 23 mmol) in dichloromethane (10 mL) was added over a period of 15 minutes. The resulting mixture was stirred at 0° C. for 8 hours, and at room temperature overnight. The product mixture was concentrated under vacuum, and the residue was subjected to column chromatography on silica gel eluted with 40-50% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided tert-butyl N-(ethenesulfonyl)glycinate.

Workup

  1. additionwas added over a period of 15 minutes
  2. customat room temperature
  3. customovernight
  4. concentrationThe product mixture was concentrated under vacuum
  5. washeluted with 40-50% ethyl acetate in hexane
  6. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-7379b2691d014433b6074fdc78c21309
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

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