(R)-N-(4-methoxybenzyl)glutamic acid

Base Information

Chemical Name:(R)-N-(4-methoxybenzyl)glutamic acid
CAS No.:73915-05-6
Molecular Formula:C₁₃H₁₇NO₅
Molecular Weight:267.282
Hs Code.:

Synonyms:

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Chemical Property of (R)-N-(4-methoxybenzyl)glutamic acid

Chemical Property:

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Technology Process of (R)-N-(4-methoxybenzyl)glutamic acid

There total 1 articles about (R)-N-(4-methoxybenzyl)glutamic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 39.0%

: 6893-26-1,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
D-Glutamic acid

: 123-11-5
4-methoxy-benzaldehyde

: 73915-05-6
(R)-N-(4-methoxybenzyl)glutamic acid

Guidance literature:: With sodium hydroxide; sodium tetrahydroborate; In water; for 3.5h; Ambient temperature;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 73915-05-6
(R)-N-(4-methoxybenzyl)glutamic acid

: 159580-69-5
(2S,3S,5R)-5-Benzyloxymethyl-2-formyl-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1: 83 percent / thionyl chloride / 3 h / Heating

2: 92 percent / lithium chloride, sodium borohydride / ethanol; tetrahydrofuran / 2 h / Ambient temperature

3: 96 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

4: 86 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 2 h / Ambient temperature

5: 96 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

6: 97 percent / 3 h / 75 °C

7: 85 percent / 1M hydrochloric acid / tetrahydrofuran; H₂O / 1 h / Ambient temperature

8: 83 percent / sodium cyanoborohydride / tetrahydrofuran; ethanol; acetic acid / 2 h / -10 °C

9: 14 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

10: 82 percent / 1,8-diazabicyclo-<5,4,0>undec-7-ene / benzene / 20 h / Heating

11: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

12: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

13: 24 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

14: 62 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; thionyl chloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetic acid; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; paraffin; benzene;
DOI:10.1016/S0040-4020(01)80643-8

Reference yield:

: 73915-05-6
(R)-N-(4-methoxybenzyl)glutamic acid

: 159516-88-8
(2R,5S)-2-Benzyloxymethyl-5-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 83 percent / thionyl chloride / 3 h / Heating

2: 92 percent / lithium chloride, sodium borohydride / ethanol; tetrahydrofuran / 2 h / Ambient temperature

3: 96 percent / NaH / dimethylformamide; paraffin / 1 h / Ambient temperature

4: 86 percent / ammonium cerium(IV) nitrate / acetonitrile; H₂O / 2 h / Ambient temperature

5: 96 percent / 4-dimethylaminopyridine / acetonitrile; triethylamine / 3 h / Ambient temperature

6: diisobutylaluminium hydride / hexane; tetrahydrofuran / 1 h / -78 °C

7: pyridinium p-toluenesulfonate / 3 h / Ambient temperature

8: 68 percent / boron trifluoride etherate / CH₂Cl₂ / 1 h / -78 °C

9: 62 percent / diisobutylaluminium hydride / toluene / 1 h / -78 °C

10: 1.) potassium carbonate; 2.) sodium borohydride / 1.) methanol, reflux, 2 h; 2.) methanol, room temp., 30 min

11: 99 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.25 h / -78 °C

With dmap; sodium tetrahydroborate; thionyl chloride; oxalyl dichloride; ammonium cerium(IV) nitrate; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; triethylamine; N,N-dimethyl-formamide; toluene; acetonitrile; paraffin;
DOI:10.1016/S0040-4020(01)80643-8