CarbaMic acid, (4-hydroxy-2-naphthalenyl)-, 1,1-diMethylethyl ester synthesis
- Product Name:CarbaMic acid, (4-hydroxy-2-naphthalenyl)-, 1,1-diMethylethyl ester
- CAS Number:139975-98-7
- Molecular formula:C15H17NO3
- Molecular Weight:259.3
![Carbonic acid, 3-[[(1,1-dimethylethoxy)carbonyl]amino]-1-naphthalenyl 1,1-dimethylethyl ester](/CAS/20210305/GIF/501440-80-8.gif)
501440-80-8
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139975-98-7
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Yield:139975-98-7 67%
Reaction Conditions:
with water;lithium hydroxide in tetrahydrofuran;methanol; for 3 h;
Steps:
1 tert-butyl (4-hydroxynaphthalen-2-yl)carbamate (23)
Diboc derivative 22 (6.5 g. 18 mmol) was dissolved in THF-MeOH-H2O (3-1-1, v/v/v, 180 mL). LiOH (650 mg, 27 mmol) was added and reaction mixture was stirred for 3 hr and then concentrated to dryness. After dilution with saturated NH4Cl, the product was extracted with EtOAc (2x100 mL). The organic layer was concentrated to dryness, dissolved in small amount of DCM and purified on 80 g a silica Teiedyne Isco column (0→20% EtOAc in hexane). Evaporation of product containing fractions afforded 3.2 g of 23 (67% yield). 1H NMR (500 MHz, CDCl3) δ: 8.07 (d, J = 8.3 Hz, 1H). 7.68 (d, J = 8.3 Hz, 1H), 7,44 (t, J= 7,3 Hz, 1H), 7,36 (m, 1H). 7.29 (s, 1H). 7.14 (br, 1H), 6.60 (br, 1H), 5,69 (br, 1H), 1.56 (s, 9H). LC/MS: retention time 2.96 min. (ESI) C15H18NO3 calculated for [M+H]+ 260; found 260.
References:
WO2018/71455,2018,A1 Location in patent:Paragraph 0011; 00241; 00245-00248
24424-99-5
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132-86-5
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139975-98-7
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24424-99-5
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90923-79-8
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139975-98-7
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24424-99-5
864 suppliers
$13.50/25G
139975-98-7
20 suppliers
inquiry