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(αS)-α-Aminocyclopentaneacetic acid

(αS)-α-Aminocyclopentaneacetic acid structure

CAS No:
2521-84-8
Formula:
C7H13NO2
Chemical Name:
(αS)-α-Aminocyclopentaneacetic acid
Synonyms:
Cyclopentaneacetic acid,α-amino-,(αS)-;Cyclopentaneacetic acid,α-amino-,L-;Cyclopentaneacetic acid,α-amino-,(S)-;(αS)-α-Aminocyclopentaneacetic acid;L-Cyclopentylglycine;(2S)-2-Amino-2-cyclopentylacetic acid;1013313-56-8
Categories:
Biochemical Engineering > Amino Acids and Derivatives

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(αS)-α-Aminocyclopentaneacetic acid Basic Attributes

Molecular Weight：

143.18

Exact Mass：

143.18

HScode：

2922499990

Characteristics

PSA：

63.3

XLogP3：

-1.5

Density：

1.1±0.1 g/cm3

Boiling Point：

276.6°C at 760 mmHg

Flash Point：

119.2±22.6 °C

Refractive Index：

1.497

Storage Conditions：

Store at 0°C

Safety Information

Precautionary statement(s)：

P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H315

(αS)-α-Aminocyclopentaneacetic acid Use and Manufacturing

Methods of Manufacturing

To a stirred solution of compound 38 (500 mg, 3.49 mmol) in 10 mL Benzene was added p-TsOH (721 mg, 4.19 mmol) and benzyl alcohol (1.08 mL, 10.5 mmol) at rt under nitrogen atmosphere. The resultant reaction mixture was then heated to reflux and continued at the same for 16 h. After completion (confirmed by TLC and LCMS), reaction mixture was concentrated under reduced pressure and resultant crude was partitioned between water [TO mL] and EtOAc (3 x 75 mL). Organic layer was separated, washed with brine and dried over sodium sulphate and concentrated under reduced pressure to afford crude compound 39 [750 mg] as pale yellow liquid. [ NMR complies].the water phase (containing 385.7 g of a sodium salt) obtained in the previous step, 13.74 g of beta-NAD+, 443.5 g of ammonium formate and 4.36 L of a crude enzyme mixed solution having a leucine dehydrogenase with a specific enzyme activity of 70 U/ml and a formate dehydrogenase with a specific enzyme activity of 35 U/ml were added to a four-neck flask, and stired to dissolve all substances to formed a mixed system, about 10 mL of strong ammonia was added to the mixed system to regulate the pH value of the mixed system to about 8, then heat the mixed system was heated to about 30 to 40 C., after reacting for 3 days, samples were tracked until conversion of the raw materials is finished, totally add 1.2 L of concentrated hydrochloric acid was totally added to the reacted system to regulate the pH value of the system to below 1, the system was passed through diatomite, and the pH of an obtained filtrate was regulated to 5 to 6 with a sodium hydroxide solution having a concentration of 50%, the system was performed suction filtration at a temperature lower than 30 C. to obtain a solid, the solid was dried and then washed with pure water having a volume which is 4 times as large as that of the solid for 2 h while stirring, then an obtained filter cake was performed suction filtration and washed with ethyl alcohol to obtain 134.6 g of a product, internal standard>97%, ee>99% and yield=40%. 1H MR(400 MHz, D2O): delta2.79 (d, 1H), 1.89(m, 1H), 1.65 to 1.43(m, 6H), 2.19(m, 2H). MS: (M+H)+=144.1.

Uses

2-Cyclopentyl-L-glycine is used in the preparation and resolution of cyclopentaneglycine.

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Guide of (αS)-α-Aminocyclopentaneacetic acid

Basic Attributes
Characteristics
Safety Information
Use and Manufacturing
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(αS)-α-Aminocyclopentaneacetic acid

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