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

Base Information

Chemical Name:(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide
CAS No.:205648-23-3
Molecular Formula:C₂₅H₃₀N₄O₄S
Molecular Weight:482.604
Hs Code.:

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

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Chemical Property of (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide

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Technology Process of (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide

There total 12 articles about (S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide 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: 59.0%

: 205648-22-2
(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-carboxamide

: 205648-23-3
(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide

Guidance literature:: With Lawessons reagent;
DOI:10.1055/s-1998-1670

Reference yield:

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

: 205648-23-3
(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide

Guidance literature:: Multi-step reaction with 12 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

With Lawessons reagent; ammonium acetate; lithium hydroxide; iodine; triethylamine; triphenylphosphine; 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;
DOI:10.1021/ja994247b

Reference yield:

: 205648-17-5
(S)-2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazole-4-carboxylic acid

: 205648-23-3
(S)-6-(benzyloxy)methyl-2-{2-[1-(tert-butoxycarbonyl)aminoethyl]-5-methyloxazol-4-yl}pyridine-3-thiocarboxamide

Guidance literature:: Multi-step reaction with 9 steps

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

2: tetrahydrofuran / 20 °C

3: 85 percent / ammonium acetate / benzene; acetic acid / 24 h / Heating

4: ethanol / 50 °C

5: 0.5 h / 140 °C

6: 92 percent / aq. LiOH / tetrahydrofuran / 20 - 45 °C

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

8: 32percent aq. NH₄OH / tetrahydrofuran / 0.75 h / -10 °C

9: 59 percent / Lawesson's reagent / benzene / 5 h / Heating

With Lawessons reagent; ammonium acetate; lithium hydroxide; triethylamine; In tetrahydrofuran; ethanol; acetic acid; benzene; 1: Carboxylation / 2: Substitution / 3: Amination / 4: Condensation / 5: Cyclization / 6: Hydrolysis / 7: Carboxylation / 8: Amination / 9: Substitution;
DOI:10.1021/ja994247b