(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
CAS No.:76284-38-3
Molecular Formula:C₂₈H₃₁N₃O₆
Molecular Weight:505.571
Hs Code.:

Synonyms:(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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Chemical Property of (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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Technology Process of (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 18 articles about (6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic 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: 92.0%

: 33125-05-2
Boc-D-Phg-OH

: (6R,7S)-7-Amino-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

: 76284-38-3
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In tetrahydrofuran;
DOI:10.1248/cpb.28.1563

Reference yield:

: 4052-69-1
penicillin-V β-sulfoxide benzyl ester

: 76284-38-3
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 131 g / trimethylphosphite, molecular sieves / toluene / 2 h / Heating

2: 48 g / 0.5N HCl / methanol / 0.25 h / Heating

3: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

4: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

5: Et₃N / CH₂Cl₂ / -78 °C

6: 10 g / Et₃N / 2 h / Ambient temperature

7: Zn / CH₂Cl₂; acetic acid

8: 2.3 g / pyridine / 0.17 h

9: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

10: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

11: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C

12: SOCl₂, pyridine / CH₂Cl₂

13: 1.58 g / CH₂Cl₂ / Heating

14: 956 mg / 10percent HCl / methanol / 1 h / Ambient temperature

15: NaIO₄, 1N H₂SO₄ / tetrahydrofuran / 1 h

16: 375 mg / Ambient temperature

17: 1.) PCl₅, 2.) MeOH

18: 92 percent / EEDQ / tetrahydrofuran

With pyridine; hydrogenchloride; methanol; sodium periodate; thionyl chloride; perchloric acid; molecular sieve; 4 A molecular sieve; phosphorus pentachloride; sulfuric acid; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; phosphorous acid trimethyl ester; In tetrahydrofuran; methanol; dichloromethane; acetic acid; toluene;
DOI:10.1248/cpb.28.1563

Reference yield:

: 68047-66-5
(R)-3-methyl-2-(2-phenoxymethyl-thiazole-4-carbonylamino)-but-3-enoic acid benzyl ester

: 76284-38-3
(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 16 steps

1: 1.) PCl₅, 2.) MeOH / 1.) r.t., 2 h, 2.) -40 deg C, r.t., 2 h

2: 1.) aq. NaHCO₃, 3.) molecular sieves (4A) / 1.) water, 2.) CH₂Cl₂, r.t., 15 min, 3.) 30 min

3: Et₃N / CH₂Cl₂ / -78 °C

4: 10 g / Et₃N / 2 h / Ambient temperature

5: Zn / CH₂Cl₂; acetic acid

6: 2.3 g / pyridine / 0.17 h

7: 14 g / 85percent mCPBA / CH₂Cl₂ / Ambient temperature

8: 1.) 30percent HClO₄, 2.) p-toluenesulfonic acid / 1.) acetone, water, r.t., 2.5 h, 2.) r.t., 1 h

9: 1.) O₃, 2.) Zn, acetic acid / 1.) CH₂Cl₂, ca. -78 deg C, 2.) -25 - -15 deg C

10: SOCl₂, pyridine / CH₂Cl₂

11: 1.58 g / CH₂Cl₂ / Heating

12: 956 mg / 10percent HCl / methanol / 1 h / Ambient temperature

13: NaIO₄, 1N H₂SO₄ / tetrahydrofuran / 1 h

14: 375 mg / Ambient temperature

15: 1.) PCl₅, 2.) MeOH

16: 92 percent / EEDQ / tetrahydrofuran

With pyridine; hydrogenchloride; methanol; sodium periodate; thionyl chloride; perchloric acid; 4 A molecular sieve; phosphorus pentachloride; sulfuric acid; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; acetic acid; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; 3-chloro-benzenecarboperoxoic acid; zinc; In tetrahydrofuran; methanol; dichloromethane; acetic acid;
DOI:10.1248/cpb.28.1563