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ChemicalBook CAS DataBase List 3-CARBOXYMETHOXY-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER
889952-83-4

3-CARBOXYMETHOXY-AZETIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER synthesis

2synthesis methods
-

Yield:-

Reaction Conditions:

Stage #1: tert-butyl 3-hydroxyazetidine-1-carboxylatewith sodium hydride in N,N-dimethyl-formamide at 0; for 0.25 h;
Stage #2: monosodium iodoacetate in N,N-dimethyl-formamide at 20; for 65 h;
Stage #3: with hydrogenchloride in water; pH=2;

Steps:

17

Preparation 17; S-Carboxymethoxyazetidine-l-carboxylic acid tert-butyl ester; Anhydrous DMF (5 mL) was added slowly to a stirred mixture of 3-hydroxyazetidine-l- carboxylic acid tert-butyl ester (350 mg, 2.0 mmol) and NaH (121 mg of a 60% dispersion in mineral oil, 3.0 mmol) at 00C. After 15 min, ICH2CO2Na (630 mg, 3.0 mmol) was added, then stirring was continued at 200C for 65 h. The solvent was removed in vacuo, then the residue was partitioned between H2O (15 mL) and EtOAc (10 mL). The organic phase was extracted with saturated aqueous Na2CO3 (2 x 10 mL), then the combined aqueous extracts were acidified to pH 2 with 2 M HCl, before being extracted with EtOAc (2 x 50 mL). The EtOAc extracts were washed with brine, before being dried (MgSO4). Filtration, solvent evaporation, and column chromatography (IH-EtOAc, 1:1) furnished the title compound

References:

WO2006/67532,2006,A1 Location in patent:Page/Page column 25

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