Triethylamine → HCID 59558653, compound

HRID 1175154Notes

Reaction equation

HRID 1175154 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:16][NH2:17])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6]1)=[O:4].C(N(CC)CC)C.[CH2:25]([O:27][C:28](=[O:33])[CH2:29][C:30](Cl)=[O:31])[CH3:26].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1([CH2:16][NH:17][C:30](=[O:31])[CH2:29][C:28]([O:27][CH2:25][CH3:26])=[O:33])[CH2:8][N:7]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:6]1)=[O:4]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 516892Sodium BicarbonateHCID 595583501-(1,1-Dimethylethyl) 3-methyl 3-(aminomethyl)-1,3-azetidinedicarboxylate

Product 1

HCID 59558653HCID 59558653, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Aminomethyl-azetidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (3.11 g; 12.7 mmol) and triethylamine (1.95 ml; 14.01 mmol) in CH2Cl2 (55 ml) are cooled to 0° C. under stirring. Chlorocarbonyl-acetic acid ethyl ester (1.9 g; 12.74 mmol) in CH2Cl2 (15 ml) is added dropwise within 15 minutes. The reaction mixture is warmed to room temperature and stirred for 30 minutes, poured on 10% aqueous NaHCO3 and extracted with CH2Cl2 three times. The combined organic phases are dried over Na2SO4, filtered, evaporated and purified via chromatography (SiO2; TBME/MeOH 97:3) to yield the title compound as colorless resin (3.8 g; 77%), which crystallizes slowly.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with CH2Cl2 three times
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. custompurified via chromatography (SiO2; TBME/MeOH 97:3)

Sources & evidence

ORD record
ord-026b2afa2af14c9d86efdc35f793ad1c
Source dataset
uspto-grants-2010_11
Patent number
US07838674B2

Reaction notes

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