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Quality Control of α-Cyclobutylglycine Purity: 97% SDS Specification

COA

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NMR

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Product Details of α-Cyclobutylglycine

CAS No. :	28024-69-3
Formula :	C₆H₁₁NO₂
M.W :	129.16
SMILES Code :	NC(C1CCC1)C(O)=O
MDL No. :	MFCD09264350
InChI Key :	FZENWFNLDOYYFB-UHFFFAOYSA-N
Pubchem ID :	14352283

Safety of α-Cyclobutylglycine

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of α-Cyclobutylglycine

* 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.

Downstream synthetic route of [ 28024-69-3 ]

[ 28024-69-3 ] Synthesis Path-Downstream 1~32

2
[ 28024-69-3 ]
cyclobutyl-2-hydroxyacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; sodium nitrite; In water; at 0 - 20℃; for 72.0h;	To <strong>[28024-69-3]2-amino-2-cyclobutylacetic acid</strong> (1 g, 6.04 mmol) in 1 M H2SO4(aq) (12 mL, 0.5 M) at0C was added 2 M NaNO2(aq) (15 mL, 30.19 mmol) slowly and the reaction was allowed to warm to rt slowly. After 3 days, 1H NMR showed no starting material and the reaction was extracted with EtOAc (3 x 50 mL). The combined organics were dried over Na2SO4 and concentrated in vacuo to afford 64a (495.0 g, 44%) as a yellow solid. 1H NMR (400 MHz, d6-DMSO): 53.78 (d, J= 8.5 Hz, 1H), 2.62 (m, 1H), 1.94 (m, 4H).
	With sulfuric acid; water; sodium nitrite; at 0 - 27℃; for 16.0h;	To a solution of <strong>[28024-69-3]2-amino-2-cyclobutylacetic acid</strong> (10.0 g, 77.5 mmol) in water (100 mL) and aqueous H2SO4 solution (0.5 M, 180 mL) at 0 C was added sodium nitrite (32 g, 465.1 mmol) and the reaction mixture warmed to RT and stirred for 16 hrs. The reaction mixture was partitioned between water and THF. The aqueous layer was four times further extracted with THF. The combined organic layers were dried (Na2SO4) and concentrated. The crude residue was washed with EtOAc and the filtrate concentrated to afford crude 2- cyclobutyl-2-hydroxyacetic acid (8.0 g, 61.5 mmol, 79 %) as a yellow liquid. This material was used without further purification.

References: [1]Patent: WO2013/185093,2013,A1 .Location in patent: Page/Page column 246.
[2]Patent: WO2021/69927,2021,A1 .Location in patent: Page/Page column 42; 59-60.

3
(S)-N-(2-benzoyl-4-chlorophenyl)-2-[3,5-dihydro-4H-dinaphth[2,1-c:1′,2′-e]azepin-4-yl]acetamide [ No CAS ]
[ 6018-89-9 ]
[ 28024-69-3 ]
C₄₃H₃₄ClN₃NiO₃ [ No CAS ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 9817 - 9830.

4
4-((1-(2-chloro-5-(trifluoromethyl)benzyl)-4-fluoropiperidin-4-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid [ No CAS ]
[ 28024-69-3 ]
2-(4-((1-(2-chloro-5-(trifluoromethyl)benzyl)-4-fluoropiperidin-4-yl)methoxy)-5-cyclopropyl-2-fluorobenzamido)-2-cyclobutylacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 20℃; for 16.0h;	To a stirred solution of 4-((1-(2-chloro-5-(trifluoromethyl)benzyl)-4-fluoropiperidin-4-yl)methoxy)-5-cyclopropyl-2-fluorobenzoic acid (0.25 g, 0.50 mmol) in tetrahydrofuran (10 mL)was added <strong>[28024-69-3]2-amino-2-cyclobutylacetic acid</strong> (0.128 g, 1.0 mmol) 1,1 ‘-carbonyldiimidazole (CDI)(0.097 g, 0.60 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (0.379 g, 2.50 mmol). Thereaction mixture was stirred at ambient temperature for 16 h then diluted with dichloromethane (50mL), washed with saturated ammonium chloride solution, brine, dried over anhydrous sodiumsulfate and concentrated in vacuo. The residue was purified by reverse phase preparative HPLC (gradient of acetonitrile in water) to afford the title compound as a colorless solid (0.054 g, 18%):‘H NMR (300 MHz, CDC13) 9.36-8.59 (br, s, 1H), 8.02 (s, 1H), 7.60-7.43 (m, 3H), 7.12 (dd, J 12.1, 7.5 Hz, 1H), 6.38 (d, J= 13.5Hz, IH), 4.56 (t, J= 7.0 Hz, 1H), 4.24-4.07 (m, 2H), 4.06-3.84(m, 2H), 3.19 (t,J= 12.8 Hz, 2H), 2.93-2.67 (m, 3H), 2.29-2.14 (m, 2H), 2.14-1.70(m, 9H),0.94-0.79 (m, 2H), 0.70-0.54 (m, 2H); MS (ES+) m/z 617.2, 615.2 (M + 1).

References: [1]Patent: WO2016/7534,2016,A1 .Location in patent: Page/Page column 219.

5
[ 28024-69-3 ]
methyl 2-(2-(diisopropylamino)-2-oxoacetamido)-2-(2-(4-methoxyphenyl)cyclobutyl)acetate [ No CAS ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 5681 - 5689.

6
[ 28024-69-3 ]
methyl 2-cyclobutyl-2-(2-(diisopropylamino)-2-oxoacetamido)acetate [ No CAS ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 5681 - 5689.

7
[ 67-56-1 ]
[ 28024-69-3 ]
C₇H₁₃NO₂ [ No CAS ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 5681 - 5689.

8
aminocyclobutylacetonitrile [ No CAS ]
[ 28024-69-3 ]

Yield	Reaction Conditions	Operation in experiment
75.9%	With hydrogenchloride; water; at 80℃; for 6.0h;	In a three-necked flask, 300 mL of 6M hydrochloric acid and 30. 0 g of aminocyclobutylacetonitrile were added and the temperature was increased to 100 C for 6 hours. Into the sodium carbonate to adjust the pH of 8, filtered temperature, the filter cake dried to amino cyclobutylacetic acid 26. 7g (75.9%).

References: [1]Patent: CN103880768,2016,B .Location in patent: Paragraph 0028-0029.

9
[ 2987-17-9 ]
[ 28024-69-3 ]

References: [1]Patent: CN103880768,2016,B .

10
[ 28024-69-3 ]
N-(1-cyclobutyl-2-hydroxyethyl)chloropropionamide [ No CAS ]

References: [1]Patent: CN103880768,2016,B .

11
[ 28024-69-3 ]
5-cyclobutylmorpholin-3-one [ No CAS ]

References: [1]Patent: CN103880768,2016,B .

12
[ 28024-69-3 ]
3-cyclobutylmorpholine [ No CAS ]

References: [1]Patent: CN103880768,2016,B .

13
[ 28024-69-3 ]
ethyl 2-cyclobutyl-2-chloropropionamidoacetate [ No CAS ]

References: [1]Patent: CN103880768,2016,B .

14
[ 64-17-5 ]
[ 28024-69-3 ]
aminocyclobutylacetic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57.8%	With hydrogenchloride;Reflux;	250 mL of an ethanolic solution of hydrochloric acid and 25. 0 g of aminocyclobutylacetic acid were added to a three-necked flask and reacted in a reflux state. After completion of the reaction, the reaction mixture was concentrated, and 200 mL of dichloromethane was added. The mixture was washed with saturated sodium hydrogencarbonate and washed with brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to give 17.6 g (57.8%) of ethylcyclobutylacetic acid ethyl ester.

References: [1]Patent: CN103880768,2016,B .Location in patent: Paragraph 0030-0031.

15
[ 28024-69-3 ]
2-cyclobutyl-2-phthalimido-2-fluoro-N-(pyridin-2-yl)acetamide [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 7100 - 7103.

16
[ 28024-69-3 ]
2-cyclobutyl-2-phthalimido-N-(pyridin-2-yl)acetamide [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 7100 - 7103.

17
[ 85-44-9 ]
[ 28024-69-3 ]
C₁₄H₁₃NO₄ [ No CAS ]

References: [1]Organic Letters,2018,vol. 20,p. 7100 - 7103.

18
(R)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidin-2-carboxamide [ No CAS ]
nickel diacetate [ No CAS ]
[ 28024-69-3 ]
nickel(II)-(R)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide/(R)-2-cyclobutylglycine Schiff base complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate; In methanol; at 60℃; for 16.0h;	General procedure: A suspension of (S)-4 or (R)-4 (100.3 mg, 0.2 mmol, 1 equiv.), rac-phenylalanine 5a (33 mg, 0.2mmol, 1 equiv.), Ni(OAc)2 (35.3 mg, 0.2 mmol, 1 equiv.), and K2CO3 (138.1 mg, 1.0 mmol, 5 equiv.) were refluxed in methanol (4 mL) at 60 C for 8 h. After cooling to room temperature, the mixture was diluted with 5% aqueous acetic acid (15 mL) and extracted three times with dichloromethane.The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude mixture was purified by column chromatography on silica gel (PE/EA = 4:1 to DCM/MeOH =20:1) to afford two diastereomers (S,2S)-6a and (S,2R)-6a (138 mg, yield 98%) for analysis (dr > 99:1). The mixture was purified again by column chromatography on silica gel (DCM/MeOH = 40:1) to givethe pure diastereomer (S,2S)-6a as a red solid.

References: [1]Molecules,2019,vol. 24.

19
(S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide [ No CAS ]
nickel diacetate [ No CAS ]
[ 28024-69-3 ]
nickel(II)-(S)-N-(2-benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)-2-methylpyrrolidine-2-carboxamide/(S)-2-cyclobutylglycine Schiff base complex [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium carbonate; In methanol; at 60℃; for 16.0h;	General procedure: A suspension of (S)-4 or (R)-4 (100.3 mg, 0.2 mmol, 1 equiv.), rac-phenylalanine 5a (33 mg, 0.2mmol, 1 equiv.), Ni(OAc)2 (35.3 mg, 0.2 mmol, 1 equiv.), and K2CO3 (138.1 mg, 1.0 mmol, 5 equiv.) were refluxed in methanol (4 mL) at 60 C for 8 h. After cooling to room temperature, the mixture was diluted with 5% aqueous acetic acid (15 mL) and extracted three times with dichloromethane.The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude mixture was purified by column chromatography on silica gel (PE/EA = 4:1 to DCM/MeOH =20:1) to afford two diastereomers (S,2S)-6a and (S,2R)-6a (138 mg, yield 98%) for analysis (dr > 99:1). The mixture was purified again by column chromatography on silica gel (DCM/MeOH = 40:1) to givethe pure diastereomer (S,2S)-6a as a red solid.

References: [1]Molecules,2019,vol. 24.

20
[ 28024-69-3 ]
methyl 4-(1-(2-cyclobutyl-2-((3-(methylsulfonyl)benzyl)oxy)acetamido)cyclopropyl)benzoate [ No CAS ]