ChemicalBook CAS DataBase List cis-4-Hydroxy-L-proline

cis-4-Hydroxy-L-proline synthesis

10synthesis methods

Product Name:cis-4-Hydroxy-L-proline
CAS Number:618-27-9
Molecular formula:C5H9NO3
Molecular Weight:131.13

13504-86-4 Synthesis

13504-86-4
85 suppliers
$18.00/100mg

618-27-9
305 suppliers
$9.00/250mg

Yield:618-27-9 87%

Reaction Conditions:

with hydrogenchloride in water at 80; for 1 h;

Steps:

1-2; 1 Comparative Example 1
50.0 g (0.19 mol) of cis-benzyloxycarbonyl-4-hydroxy-L-proline obtained in the same manner as in Reference Example 4, 166.1 g of water and 196.4 g of concentrated hydrochloric acid , Heated to 80 ° C. and reacted for 1 hour. As a result, the conversion of cis-benzyloxycarbonyl-4-hydroxy-L-proline was 99.1%. To the reaction solution, 30.4 g of toluene was added and the layers were separated. 382.8 g of the separated aqueous layer was concentrated under conditions of 50 ° C. and 5 kPa to obtain 216.8 g of concentrated liquid. 38.7 g of 48% sodium hydroxide aqueous solution was added dropwise to the slurry to neutralize to pH 6.8, and further concentrated under reduced pressure of 5 kPa to obtain 112.8 g of slurry. 245.3 g of methanol was added to the resulting slurry and aged at 10 ° C. for 14 hours to precipitate cis-4-hydroxy-L-proline. The aged slurry was subjected to solid-liquid separation with a centrifugal dehydrator to obtain 31.9 g of moisture-containing cake, further vacuum dried at 40 ° C. under 2 kPa for 5 hours, and dried cake 26.4 g I got it. 15.0 g of cis-4-hydroxy-L-proline in the dried cake 26.4 and 11.4 g of sodium chloride were contained. Further, in order to recover cis-4-hydroxy-L-proline from the mother liquor during solid-liquid separation, the whole mother liquor was concentrated to 26.7 g, 33.0 g of methanol was further added and aged at 10 ° C. for 12 hours to obtain slurry Filtration was carried out to obtain 20.0 g of a cake containing moisture. Further, it was vacuum dried at 40 ° C. under 2 kPa or less for 5 hours to obtain 17.1 g of dried cake. 6.6 g of cis-4-hydroxy-L-proline in the dried cake 17.1 and 10.5 g of sodium chloride were contained. The yield of cis-4-hydroxy-L-proline including cis-4-hydroxy-L-proline recovered from the mother liquor was 87.0%, but a large amount of sodium chloride as an inorganic salt was contained

References:

TORAY FINE CHEMICALS COMPANY LIMITED;NISHIMURA, TOMOAKI;MORIMOTO, MASAO JP5703654, 2015, B2 Location in patent:Paragraph 00056-0062; 0065; 0066

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147-85-3 Synthesis