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Quality Control of H-Cyclopropyl-Ala-OH Purity: 97% SDS Specification

COA

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NMR

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Product Details of H-Cyclopropyl-Ala-OH

CAS No. :	102735-53-5
Formula :	C₆H₁₁NO₂
M.W :	129.16
SMILES Code :	O=C(O)[C@@H](N)CC1CC1
Synonyms :	(S)-2-Amino-3-cyclopropylpropanoic acid
MDL No. :	MFCD00798687
InChI Key :	XGUXJMWPVJQIHI-YFKPBYRVSA-N
Pubchem ID :	6951383

Safety of H-Cyclopropyl-Ala-OH

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

Application In Synthesis of H-Cyclopropyl-Ala-OH

* 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 [ 102735-53-5 ]

[ 102735-53-5 ] Synthesis Path-Downstream 1~35

1
[ 102693-69-6 ]
[ 102735-53-5 ]

References: [1]Chemistry Letters,1986,p. 511 - 512.

2
[ 102735-53-5 ]
[ 61-90-5 ]
[ 327-57-1 ]

References: [1]Chemistry Letters,1986,p. 511 - 512.

3
[ 133992-69-5 ]
[ 121786-39-8 ]
[ 102735-53-5 ]
[ 121786-36-5 ]
[ 121703-93-3 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 6354 - 6364.
[2]Journal of the American Chemical Society,1989,vol. 111,p. 6354 - 6364.

4
[ 133992-69-5 ]
[ 102735-53-5 ]
[ 121786-36-5 ]

References: [1]Journal of the American Chemical Society,1989,vol. 111,p. 6354 - 6364.

5
[ 133992-69-5 ]
[ 102735-53-5 ]

References: [1]Synthetic Communications,1996,vol. 26,p. 1109 - 1115.

6
[ 102735-53-5 ]
[ 530-62-1 ]
[ 766-17-6 ]
[ 177913-96-1 ]

References: [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 2313 - 2330.

7
[ 102735-53-5 ]
Pseudomonas spp. MK₉₁CC₈ marine tube isolate [ No CAS ]
C₅₄H₉₃N₉O₁₆ [ No CAS ]

References: [1]Journal of Natural Products,1997,vol. 60,p. 223 - 229.

8
[ 102735-53-5 ]
[ 300853-97-8 ]

Yield	Reaction Conditions	Operation in experiment
4.30 g (85%)	With sulfuric acid; sodium nitrite; In water;	Step A 2-(S)-Hydroxy-3-(cyclopropyl)propanoic acid A 1 L, 3-neck flask was equipped with two dropping funnels, one containing 21.3 mL of 2.0 N H2SO4 and the other containing 21.3 mL of 2.0 N NaNO2. A mixture of 5.00 g (38.7 mmol) of 2-(S)amino-3-(cyclopropyl)propanoic acid in 28 mL of H2O at 0° C. was treated with a sufficient amount of the acid solution to dissolve the solid. The remaining H2SO4 solution and the NaNO2 solution were added, maintaining the internal temperature at less than 5° C. The resulting mixture was stirred cold for 3 h, then warned to rt and stirred for 20 h. The reaction mixture was saturated with NaCl and extracted with 4*100 mL of EtOAc. The extracts were dried over MgSO4 and concentrated to afford 4.30 g (85percent) of the title compound: 1H NMR (300 MHz) delta 0.13-0.18 (m, 2H), 0.48-0.54 (m, 2H), 0.89 (m, 1H), 1.67-1.76 (m, 2H), 4.37 (dd, J=6.4, 4.7 Hz, 1H).

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 3001 - 3004.
[2]Patent: US6265434,2001,B1 .

9
[ 102735-53-5 ]
[ 115-11-7 ]
[ 457059-27-7 ]

Yield	Reaction Conditions	Operation in experiment
4.2 g (84%)	With sulfuric acid; In 1,4-dioxane;	3a (S)-beta-Cyclopropylalanine Tert-Butyl Ester 3.5 g (27.1 mmol) of (S)-beta-cyclopropylalanine were added to a mixture of 50 mL of dioxane and 5 ml of concentrated sulfuric acid (prepared by cautious addition of the acid dropwise to dioxane at 5° C.) at room temperature. The solution was transferred into a sealing tube into which 40 ml of isobutylene were condensed at -78° C. The sealed tube was then shaken at room temperature on a shaker for 24 hours. After the sealed tube had been opened (while cooling), the reaction mixture was cautiously introduced into a stirred mixture of 30 mL of triethylamine and 50 mL of water cooled to 0° C. After removal of excess isobutylene, the product was extracted with ether (2*50 mL). Drying of the ether phases over magnesium sulfate, filtration and removal of the solvent in vacuo resulted in the crude product (pale yellow oil), which was employed without further purification in the subsequent reaction. Yield 4.2 g (84percent). 1H NMR (CDCl3): delta 0.10 (m, 2H, CH2), delta 0.49 (m, 2H, CH2), delta 0.81 (m, 1H, CH), delta 1.25 (br. m, 2H, NH2), delta 1.50 (s, 9H, (CH3)3), delta 1.61 (m, 2H, CH2), delta 3.41 ppm (dd, 1H, N-CH)

References: [1]Tetrahedron,2004,vol. 60,p. 4295 - 4302.
[2]Patent: US2002/183374,2002,A1 .

10
[ 113741-17-6 ]
[ 102735-53-5 ]

References: [1]Tetrahedron Asymmetry,2003,vol. 14,p. 3575 - 3580.
[2]Organic Letters,2002,vol. 4,p. 2421 - 2424.

11
[ 102735-53-5 ]
[ 710334-45-5 ]