2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

Base Information

Chemical Name:2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester
CAS No.:157848-27-6
Molecular Formula:C₂₄H₃₁N₅O₆S
Molecular Weight:517.606
Hs Code.:

Synonyms:2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

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Chemical Property of 2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

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Technology Process of 2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

There total 12 articles about 2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester 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:

: 619-44-3
methyl 4-iodobenzoate

: 157848-27-6
2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: CuI, (Ph₃P)2PdCl₂ / diethylamine / Ambient temperature

2: H₂ / 5percent Pd-C / ethanol / 3.5 h / 2327.2 Torr

3: Et₃N / CH₂Cl₂ / 0.83 h / 0 °C

4: aq. TFA / CH₂Cl₂ / 24 h / Heating

5: diisopropylethylamine / dimethylformamide / 3 h / Ambient temperature

6: pyridinium p-toluenesulfonate / benzene / 3 h / Heating

7: 1.) Hg(OAc)2, TFA, 2.) H₂S, MeOH, 3.) NaBH₄

8: diisopropylethylamine / dimethylformamide / 0.5 h / 100 °C

9: 98 percent / 2N aq. HCl / tetrahydrofuran / 2.5 h / Heating

10: 50 percent / BF₃*Et₂O, NaBH₃CN / tetrahydrofuran / 0.5 h

11: 1N aq. NaOH / Ambient temperature

12: HOBT, diisopropylethylamine, EDC / dimethylformamide / 18 h

With hydrogenchloride; methanol; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium tetrahydroborate; copper(l) iodide; boron trifluoride diethyl etherate; hydrogen sulfide; mercury(II) diacetate; hydrogen; pyridinium p-toluenesulfonate; sodium cyanoborohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; diethylamine; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm9607459

Reference yield:

: 157848-16-3
4-(3-hydroxy-4,4-dimethoxybut-1-ynyl)benzoic acid methyl ester

: 157848-27-6
2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 11 steps

1: H₂ / 5percent Pd-C / ethanol / 3.5 h / 2327.2 Torr

2: Et₃N / CH₂Cl₂ / 0.83 h / 0 °C

3: aq. TFA / CH₂Cl₂ / 24 h / Heating

4: diisopropylethylamine / dimethylformamide / 3 h / Ambient temperature

5: pyridinium p-toluenesulfonate / benzene / 3 h / Heating

6: 1.) Hg(OAc)2, TFA, 2.) H₂S, MeOH, 3.) NaBH₄

7: diisopropylethylamine / dimethylformamide / 0.5 h / 100 °C

8: 98 percent / 2N aq. HCl / tetrahydrofuran / 2.5 h / Heating

9: 50 percent / BF₃*Et₂O, NaBH₃CN / tetrahydrofuran / 0.5 h

10: 1N aq. NaOH / Ambient temperature

11: HOBT, diisopropylethylamine, EDC / dimethylformamide / 18 h

With hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen sulfide; mercury(II) diacetate; hydrogen; pyridinium p-toluenesulfonate; sodium cyanoborohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm9607459

Reference yield:

: 157848-17-4
4-(3-hydroxy-4,4-dimethoxybutyl)benzoic acid methyl ester

: 157848-27-6
2(S)-({4-[2-(2-amino-4-oxo-4,6,7,8-tetrahydro-3H-pyrimido[5,4-b][1,4]thiazin-6-yl)ethyl]benzoyl}amino)pentanedioic acid diethyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃N / CH₂Cl₂ / 0.83 h / 0 °C

2: aq. TFA / CH₂Cl₂ / 24 h / Heating

3: diisopropylethylamine / dimethylformamide / 3 h / Ambient temperature

4: pyridinium p-toluenesulfonate / benzene / 3 h / Heating

5: 1.) Hg(OAc)2, TFA, 2.) H₂S, MeOH, 3.) NaBH₄

6: diisopropylethylamine / dimethylformamide / 0.5 h / 100 °C

7: 98 percent / 2N aq. HCl / tetrahydrofuran / 2.5 h / Heating

8: 50 percent / BF₃*Et₂O, NaBH₃CN / tetrahydrofuran / 0.5 h

9: 1N aq. NaOH / Ambient temperature

10: HOBT, diisopropylethylamine, EDC / dimethylformamide / 18 h

With hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; boron trifluoride diethyl etherate; hydrogen sulfide; mercury(II) diacetate; pyridinium p-toluenesulfonate; sodium cyanoborohydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/jm9607459