2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

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Chemical Name:2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid
CAS No.:216481-08-2
Molecular Formula:C₂₈H₃₀N₄O₆S
Molecular Weight:550.635
Hs Code.:

Synonyms:2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

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Chemical Property of 2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

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Technology Process of 2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

There total 15 articles about 2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic 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: 94.0%

: 205648-24-4
(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}-3-(4-ethoxycarbonylthiazol-2-yl)pyridine

: 216481-08-2
2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

Guidance literature:: With lithium hydroxide; water; In tetrahydrofuran;
DOI:10.1039/a805762a

Reference yield:

: 78981-25-6,81587-17-9,85642-13-3
tert-butyl (1S)-2-amino-1-methyl-2-oxoethylcarbamate

: 216481-08-2
2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 15 steps

1: 80 percent / dirhodium(II) acetate / CHCl₃ / Heating

2: 70 percent / triethylamine; triphenylphosphine; iodine / CH₂Cl₂ / 20 °C

3: 95 percent / aq. LiOH / methanol / 5 h / 20 °C

4: triethylamine / tetrahydrofuran / 0.33 h / 0 °C

5: tetrahydrofuran / 20 °C

6: 85 percent / ammonium acetate / benzene; acetic acid / 24 h / Heating

7: ethanol / 50 °C

8: 0.5 h / 140 °C

9: 92 percent / aq. LiOH / tetrahydrofuran / 20 - 45 °C

10: triethylamine / tetrahydrofuran / 0.83 h / -10 °C

11: 32percent aq. NH₄OH / tetrahydrofuran / 0.75 h / -10 °C

12: 59 percent / Lawesson's reagent / benzene / 5 h / Heating

13: potassium hydrogen carbonate / tetrahydrofuran / 16 h / -3 °C

14: trifluoroacetic anhydride; 2,6-lutidine / tetrahydrofuran / 3 h / 0 °C

15: 94 percent / aq. LiOH / tetrahydrofuran / 20 °C

With Lawessons reagent; 2,6-dimethylpyridine; ammonium acetate; lithium hydroxide; iodine; potassium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic anhydride; dirhodium tetraacetate; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; acetic acid; benzene; 1: Condensation / 2: Cyclization / 3: Hydrolysis / 4: Carboxylation / 5: Substitution / 6: Amination / 7: Condensation / 8: Cyclization / 9: Hydrolysis / 10: Carboxylation / 11: Amination / 12: Substitution / 13: Condensation / 14: Cyclization / 15: Hydrolysis;
DOI:10.1021/ja994247b

Reference yield:

: 205648-15-3
N-(tert-butoxycarbonyl)-N'-[2-(1-methoxycarbonyl-3-oxobutyl)]-S-alaninamide

: 216481-08-2
2-{6-Benzyloxymethyl-2-[2-((S)-1-tert-butoxycarbonylamino-ethyl)-5-methyl-oxazol-4-yl]-pyridin-3-yl}-thiazole-4-carboxylic acid

Guidance literature:: Multi-step reaction with 14 steps

1: 70 percent / triethylamine; triphenylphosphine; iodine / CH₂Cl₂ / 20 °C

2: 95 percent / aq. LiOH / methanol / 5 h / 20 °C

3: triethylamine / tetrahydrofuran / 0.33 h / 0 °C

4: tetrahydrofuran / 20 °C

5: 85 percent / ammonium acetate / benzene; acetic acid / 24 h / Heating

6: ethanol / 50 °C

7: 0.5 h / 140 °C

8: 92 percent / aq. LiOH / tetrahydrofuran / 20 - 45 °C

9: triethylamine / tetrahydrofuran / 0.83 h / -10 °C

10: 32percent aq. NH₄OH / tetrahydrofuran / 0.75 h / -10 °C

11: 59 percent / Lawesson's reagent / benzene / 5 h / Heating

12: potassium hydrogen carbonate / tetrahydrofuran / 16 h / -3 °C

13: trifluoroacetic anhydride; 2,6-lutidine / tetrahydrofuran / 3 h / 0 °C

14: 94 percent / aq. LiOH / tetrahydrofuran / 20 °C

With Lawessons reagent; 2,6-dimethylpyridine; ammonium acetate; lithium hydroxide; iodine; potassium hydrogencarbonate; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; ethanol; dichloromethane; acetic acid; benzene; 1: Cyclization / 2: Hydrolysis / 3: Carboxylation / 4: Substitution / 5: Amination / 6: Condensation / 7: Cyclization / 8: Hydrolysis / 9: Carboxylation / 10: Amination / 11: Substitution / 12: Condensation / 13: Cyclization / 14: Hydrolysis;
DOI:10.1021/ja994247b