(2S)-1-[(tert-butoxy)carbonyl]-2-methylazetidine-2-carboxylic acid synthesis
- Product Name:(2S)-1-[(tert-butoxy)carbonyl]-2-methylazetidine-2-carboxylic acid
- CAS Number:1363402-35-0
- Molecular formula:C10H17NO4
- Molecular Weight:215.25
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Yield:1363402-35-0 93%
Reaction Conditions:
Stage #1: (S)-2-methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterwith sodium hydroxide in tetrahydrofuran;water at 60; for 1 h;Inert atmosphere;
Stage #2: with hydrogenchloride in tetrahydrofuran;water; pH=1;
Steps:
4.4.8. (S)-2-Methyl-azetidine-1,2-dicarboxylic acid 1-tert-butyl ester 13
To a solution of (S)-12 (0.250 g, 1.09 mmol) in THF (13 mL) and methanol (7 mL) was added a solution of sodium hydroxide (0.087 g, 2.17 mmol) in water (1.3 mL). After stirring at 60 °C for 1 h, water (50 mL) was added to the reaction mixture and the organic solvents were evaporated. The aqueous layer was washed with ether (4 × 10 mL) and acidified to pH 1 with a 0.5 M HCl aqueous solution (5 mL). The aqueous layer was extracted with ether (4 × 25 mL). The organic layer was dried over magnesium sulfate and evaporated to dryness. Compound 13 was obtained as a white solid (0.209 g, 93%). Rf: 0.40 (DCM/methanol 90/10), Mp: 99 °C, (c 0.5, CH2Cl2), 1H NMR (300 MHz, CDCl3): δ = 1.48 (s, 9H, tBu), 1.72 (s, 3H, CH3), 2.02-2.11 (m, 1H, H-3), 2.71-2.80 (m, 1H, H-3'), 3.75-3.90 (m, 2H, H-4, H-4'), 8.51-10.56 (s, 1H, COOH) ppm. 13C NMR (75 MHz, CDCl3): δ = 22.2 (CH3), 27.6 (C-3), 28.3 (tBu), 44.5 (C-4), 69.1 (C-2), 82.6 (Cq), 157.3, 174.8 (CO) ppm. IR (ATR) νmax 2973, 2931, 2896, 2653, 2552, 1723, 1622, 1455, 1431, 1366, 1282, 1252, 1160, 1085, 860, 769, 778, 716 cm-1; ESIHRMS (positive mode) m/z calcd for C12H17NO4Na [M+Na]+: 238.1055, found 238.1059.
References:
Drouillat, Bruno;Wright, Karen;Marrot, Jerome;Couty, Francois [Tetrahedron Asymmetry,2012,vol. 23,# 9,p. 690 - 696] Location in patent:experimental part
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