(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

Base Information

Chemical Name:(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester
CAS No.:68047-65-4
Molecular Formula:C₂₃H₂₄N₂O₅S
Molecular Weight:440.52
Hs Code.:

(<i>R</i>)-2-[(2<i>R</i>)-2<i>r</i>-mercapto-4-oxo-3<i>c</i>-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

Synonyms:(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

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Chemical Property of (R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

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Technology Process of (R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

There total 1 articles about (R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl 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:

: 68047-65-4
(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

Guidance literature:: Thiazolin 2, HCl, Me.;
DOI:10.1039/c39780000239

Reference yield:

: 68047-65-4
(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

: 75029-93-5
(2R,6R,7R)-3-Hydroxy-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid

Guidance literature:: Multi-step reaction with 13 steps

1: pyridine / CH₂Cl₂

2: 100 percent / Et₃N / benzene

3: 77 percent / O₃ / ethyl acetate / -78 °C

4: NaBH₄, AcOH / tetrahydrofuran / 0 °C

5: SOCl₂, 2,6-lutidine / CH₂Cl₂ / -35 - 0 °C

6: NaN₃ / dimethylformamide / 0 °C

7: H₂ / Pd/C / formic acid

8: acetic acid / 0 °C

9: 86 percent / POCl₃, 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 48 percent / Zn-dust, AcOH / dimethylformamide / 0 °C

11: 88 percent / Al/Hg / tetrahydrofuran; H₂O / 5 - 10 °C

12: 45 percent / CuSO₄*5H₂O / aq. acetic acid

13: 69 percent / Na₂CO₃ / tetrahydrofuran; H₂O

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; aluminum amalgam; thionyl chloride; sodium azide; hydrogen; sodium carbonate; ozone; copper(II) sulfate; acetic acid; triethylamine; zinc; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; formic acid; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00539a046

Reference yield:

: 68047-65-4
(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

: 75029-89-9
(6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: pyridine / CH₂Cl₂

2: 100 percent / Et₃N / benzene

3: 77 percent / O₃ / ethyl acetate / -78 °C

4: NaBH₄, AcOH / tetrahydrofuran / 0 °C

5: SOCl₂, 2,6-lutidine / CH₂Cl₂ / -35 - 0 °C

6: NaN₃ / dimethylformamide / 0 °C

7: H₂ / Pd/C / formic acid

8: acetic acid / 0 °C

9: 86 percent / POCl₃, 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 48 percent / Zn-dust, AcOH / dimethylformamide / 0 °C

11: 88 percent / Al/Hg / tetrahydrofuran; H₂O / 5 - 10 °C

12: 68 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

13: 69 percent / DBU / CH₂Cl₂ / -20 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; aluminum amalgam; thionyl chloride; sodium azide; hydrogen; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; formic acid; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00539a046