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Chemical Structure| 22818-40-2 Chemical Structure| 22818-40-2
Chemical Structure| 22818-40-2

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CAS No.: 22818-40-2

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H-D-Phg(4-OH)-OH is an essential intermediate in the production of semi-synthetic β-lactam antibiotics, such as amoxicillin and cefadroxil.

Synonyms: 4-Hydroxy-D-phenylglycine; D-(-)-4-Hydroxyphenylglycine; D-4-Hydroxyphenylglycine

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Product Details of H-D-Phg(4-OH)-OH

CAS No. :22818-40-2
Formula : C8H9NO3
M.W : 167.16
SMILES Code : O=C(O)[C@H](N)C1=CC=C(O)C=C1
Synonyms :
4-Hydroxy-D-phenylglycine; D-(-)-4-Hydroxyphenylglycine; D-4-Hydroxyphenylglycine
MDL No. :MFCD00004262
InChI Key :LJCWONGJFPCTTL-SSDOTTSWSA-N
Pubchem ID :89853

Safety of H-D-Phg(4-OH)-OH

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

Application In Synthesis of H-D-Phg(4-OH)-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 [ 22818-40-2 ]

[ 22818-40-2 ] Synthesis Path-Downstream   1~6

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YieldReaction ConditionsOperation in experiment
With hydrogenchloride; C15H13O4S(1-)*K(1+); C15H12ClO4S(1-)*K(1+); In water; isopropyl alcohol;Resolution of racemate; Resolutions Performed with Potassium Chalcon-sulfonates IGeneral Procedure[0061] The sulfonate or mixture of sulfonates (1 mmol) obtained in example 14 was suspended in 1,0 mL 10percent HCl. The racemate was added (1 mmol) and 1 mL of iPrOH. The mixture was heated until clear. The salt was removed by filtration under suction and washed with little iPrOH. The salt was analyzed by HPLC to determine the e.e. The results are depicted in the following table. The values in parentheses are after recrystallization. Yields are calculated with respect to the racemate.[0062] Resolution of DL-leucine[0063] with a (1:1:1) mixture of Ia, Ib and Ic; ee=99percent; yield=14percent.[0064] Resolution of DL-phenylglycine[0065] with a (1:1) mixture of Ia and If; ee=80percent (94percent); yield 66percent[0066] with a (1:1) mixture of Ib and Id; ee=70percent (96percent); yield (12percent)[0067] with a (1:1) mixture of If and Ih; ee=57percent[0068] with Ib; ee=24percent; yield=46percent[0069] Resolution of DL-p-methyl-[alpha]-methylbenzylamine[0070] with a (1:1:1) mixture of Ia, Ib and Ic; ee=60percent; yield=30percent[0071] with Ib; ee 22percent; yield>50percent[0072] Resolution of DL-p-hydroxyphenylglycine[0073] with a (1:1) mixture of Ia and If; ee=49percent; yield 22percent.
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YieldReaction ConditionsOperation in experiment
83.5% With sodium carbonate; zinc dibromide; In water; at 200℃; for 3h;Autoclave; In 1L three-necked flask were successively added water 800ml, sodium carbonate 56g, stir, added in portions D-(-)-α-hydroxyphenylglycine 83.6g, stirring until completely dissolved, transferred in its entirety to a 2L autoclave within , was added 4-ethyl-2,3-bis-oxo-piperazine-1-carbonyl chloride 105g, zinc bromide, 0.7g, stir lid was closed and open stirring, the system was heated to 150 deg.] C, the reaction was continued 3h, stop stirring, cooling, opening the purge valve, decreased to atmospheric pressure, the solution was transferred to a 2L flask, concentrated out most of the methanol, the mother liquor plus active carbon, filtered and the filtrate was placed in an ice-water bath cooled solution of 6mol / L hydrochloric acid PH = 1.5, a lot of white precipitate crystallization, filtration, drying HO-EPCP pure 136.4g, a yield of 81.4%. Purity by HPLC 99.3%. Was prepared as in Example 1 except that: the condensation reaction temperature is 200 deg.] C, the condensation reaction time was 3h. The resulting HO-EPCP pure 140.1.9g, a yield of 83.5%. Purity by HPLC 97.9%.
 

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