Triethylamine → HCID 22346334, compound

HRID 897335Notes

Reaction equation

HRID 897335 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][S:14](Cl)(=[O:16])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:19][O:20][C:21](=[O:24])[CH2:22][NH2:23].C(N(CC)CC)C>ClCCl>[O:10]=[C:9]([NH:11][CH2:12][CH2:13][S:14](=[O:16])(=[O:15])[NH:23][CH2:22][C:21]([O:20][CH3:19])=[O:24])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 13255033Benzyl [2-(chlorosulfonyl)ethyl]carbamate

Product 1

HCID 22346334HCID 22346334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A cold (0° C.) mixture of sulfonyl chloride from Step 1 (5.54 g, 20 mmol) and glycine methyl ester hydrochloride (2.7 g, 21.5 mmol) in dichloromethane (125 mL) was treated with triethylamine (6.0 mL, 43 mmol). The resultant mixture was stirred at 0° C. for 2 hours. The product mixture was diluted with dichloromethane and was washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with 50% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the intermediate methyl 3-oxo-1-phenyl-2-oxa-7-thia-4,8-diazadecan-10-oate 7,7-dioxide.

Workup

  1. washwas washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. washeluted with 50% ethyl acetate in hexane
  6. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-eff684a23d0b4b948849634e2b647397
Source dataset
uspto-grants-2005_07
Patent number
US06921759B2

Reaction notes

Loading…