Hydrochloric Acid → 1-(tert-Butoxycarbonyl)-3-(ethoxycarbonyl)azetidine-3-carboxylic acid

HRID 1175125Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C:17]([O:19]CC)=[O:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:7]1)=[O:5])[CH3:2].[OH-].[Na+].Cl>CCO.O>[CH2:1]([O:3][C:4]([C:6]1([C:17]([OH:19])=[O:18])[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 50 °C

Procedure

Azetidine-1,3,3-tricarboxylic acid 1-tert-butyl ester 3,3-diethyl ester (1.2 g; 0.4 mmol) in EtOH (12 ml) is cooled to 5° C. under stirring and combined with NaOH (60 mg; 0.04 mmol) in water (4 ml). The reaction mixture is left at room temperature for 1 hour, heated to 50° C. for 5 minutes, poured on brine, acidified with 2N HCl and extracted with TBME three times. The reaction mixture is extracted with TBME three times, the organic phases are combined, dried over Na2SO4 and evaporated to dryness, yielding the desired product as colorless crystals. 1H-NMR (400 MHz; DMSO-d6: 13.58 (bs, 1H); 4.20 (q, 2H); 4.12 (bs, 4H); 1.39 (s, 9H); 1.21 (t, 3H). MS (m/z) ES+: 274 (30; MH+); 174 (100).

Workup

additionpoured on brine
extractionextracted with TBME three times
extractionThe reaction mixture is extracted with TBME three times
dry with materialdried over Na2SO4
customevaporated to dryness

Sources & evidence

ORD record: ord-7b7fe557d6e54555857fb8942a1cfaf3
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07838674B2

Reaction notes

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