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Product Details of [ 142929-48-4 ]

CAS No. :142929-48-4 MDL No. :MFCD09751120
Formula : C9H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :HJYNLENYMULSAS-UHFFFAOYSA-N
M.W : 201.22 Pubchem ID :15000282
Synonyms :

Safety of [ 142929-48-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
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Application In Synthesis of [ 142929-48-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 142929-48-4 ]
  • Downstream synthetic route of [ 142929-48-4 ]

[ 142929-48-4 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 109-11-5 ]
  • [ 24424-99-5 ]
  • [ 142929-48-4 ]
YieldReaction ConditionsOperation in experiment
76% With dmap In tetrahydrofuran at 20℃; for 24 h; Step 1: 7¾ri-butyl 3-oxomorpholine- -carboxylate [00197] Morpholin-3-one (35g, 346.2 mmol) was slurried in dry THF (350ml). Tert- butoxycarbonyl tert- butyl carbonate (105.8g, 11 1.4 mmol) was added, followed by DMAP (4.2g, 34.6 mmol). The mixture began to degass rapidly over 30 minutes. The resulting orange solution was stirred at ambient temperature for 24hrs. The mixture was then cooled in an ice bath and imidazole (23.57g, 346.2 mmol) was added. After stirring for 30 minutes ethyl acetate (500ml) was added. The organic phase was separated and washed with 1percent (v/v) HC1 (500ml), then sat NaHC03 (500ml), then brine (200ml), dried (MgS04), filtered and concentrated. The crude was purified through a plug of silica gel, eluting with ethyl acetate. The filtrate was evaporated to give an oil. 40/60 pet ether (200ml) was added slowly with stirring to generate a white solid. The mixture was aged for 30 minutes, cooled briefly in an ice bath and filtered, washing with 40/60 pet ether. Tert-butyl 3-oxomorpholine-4- carboxylate was obtained as a white solid which was dried under vacuum (52.7g, 76percent); lH- NMR (CDCI3) 1.47 (9H, s), 3.68 (2H, m), 3.82 (2H, m), 4.15 (2H, s); MS ES(+) 145.8 (M+ - tBu).
66% With dmap In tetrahydrofuran at 20℃; Inert atmosphere Morpholmn-3-one (8.00 g, 79.2 mmcl) was dissolved in dry THE (100 mL), and then (Boc)20 (25.9 g, 0.119 mol) and DMAP (966 mg, 7.92 mmol) were added. The mixture was stirred at room temperature under N2 atmosphere overnight. Imidazole (5.39 g, 79.2 mmol) was added. After stirred for 30 mm EtOAc (150 mL) was added. The organic layer was washed with brine (100 mL), dried over Na2SO4, filtered and concentrated in vacuo to give oil whichwas solidified after standing. The solid was washed with PE (100 mL)to afford the desired compound (10.5 g, yield 66percent) as a white solid.1H NMR (300 MHz, CDCI3): 64.20 (s, 2H), 3.88-3.85 (m, 2H), 3.74-3.70 (m, 2H), 1.51 (s, 9H).LC-MS (mobile phase: from 95percent water and 5percent CH3CN to 5percent water and 95percent CH3CN in 3.0mm, purity is >95percent, Rt = 1.56 mm; MS Calcd.: 201; MS Found: 202 [M+H] 146 [M-56+H].
Reference: [1] Patent: WO2013/49719, 2013, A1, . Location in patent: Paragraph 00197
[2] Patent: WO2017/12576, 2017, A1, . Location in patent: Page/Page column 177
[3] Journal of Medicinal Chemistry, 1992, vol. 35, # 16, p. 2928 - 2938
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