ChemicalBook CAS DataBase List 4-(1-(tert-butoxycarbonylaMino)cyclobutyl)benzoic acid

4-(1-(tert-butoxycarbonylaMino)cyclobutyl)benzoic acid synthesis

6synthesis methods

Product Name:4-(1-(tert-butoxycarbonylaMino)cyclobutyl)benzoic acid
CAS Number:1259223-99-8
Molecular formula:C16H21NO4
Molecular Weight:291.34

4-(1-(tert-butoxycarbonylaMino)cyclobutyl)benzoic acid

1259223-99-8
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18107-18-1
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$33.00/5g

Benzoic acid, 4-[1-[[(1,1-dimethylethoxy)carbonyl]amino]cyclobutyl]-, methyl ester

1338243-68-7
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Yield:1338243-68-7 93%

Reaction Conditions:

with methanol in hexanes;dichloromethane at 0 - 20; for 1 h;

Steps:

5.3.1

Example 3Synthesis of tert-butyl (1-(4-(hydrazinecarbonyl)phenyl)cyclobutyl)carbamateStep 1. Synthesis of methyl 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoateTo a solution of 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoic acid (15 g, 52 mmol) in dichloromethane (200 mL) and methanol (50 mL), cooled at 0° C., was added in a dropwise manner a 2 M solution of diazomethyl trimethylsilane in hexanes (28 mL, 57 mmol). The reaction mixture was stirred at room temperature for one hour before the addition, at 0° C., of acetic acid (10 mL). The mixture was washed with saturated aqueous sodium bicarbonate solution until the aqueous phase remained basic. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo, yielding the methyl 4-(1-((tert-butoxycarbonyl)amino)cyclobutyl)benzoate as a white crystalline solid (14.8 g, 93%). M.p.=90° C.; 400 MHz ¹H NMR (DMSO-d₆) δ: 7.91 (d, J=7.6 Hz, 2H), 7.74 (s, 1H), 7.50 (d, J=8.0 Hz, 2H), 3.84 (s, 3H), 2.38 (br.s, 4H), 2.1-1.9 (m, 1H), 1.85-1.7 (m, 1H), 1.32 (br.s, 9H); LCMS [M-tBu+H]: 250.

References:

US2011/245236,2011,A1 Location in patent:Page/Page column 94

1259223-99-8
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1313883-38-3
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References

1259223-99-8
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Carbamic acid, N-[1-[4-[2-(2-amino-3-pyridinyl)-5-chloro-3H-imidazo[4,5-b]pyridin-3-yl]phenyl]cyclobutyl]-, 1,1-dimethylethyl ester

1313883-39-4
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References

1259223-99-8
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tert-butyl (1-(4-(2-(2-aminopyridin-3-yl)-5-phenyl-3H-imidazo[4,5-b]pyridin-3-yl)phenyl)cyclobutyl)carbamate

1313881-69-4
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References

1259223-99-8
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Carbamic acid, N-[1-[4-[5-[3-[4-(acetylmethylamino)-1-piperidinyl]phenyl]-2-(2-amino-3-pyridinyl)-3H-imidazo[4,5-b]pyridin-3-yl]phenyl]cyclobutyl]-, 1,1-dimethylethyl ester

1416775-98-8
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References