(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

Base Information

Chemical Name:(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester
CAS No.:372187-37-6
Molecular Formula:C₃₃H₃₇Cl₂N₃O₁₂
Molecular Weight:738.576
Hs Code.:

(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

Synonyms:(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

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Chemical Property of (1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

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Technology Process of (1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

There total 23 articles about (1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl 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:

: (1S,5R,7aR)-5-[(S)-2-(4-Benzyloxy-3,5-dichloro-benzoylamino)-2-methoxycarbonyl-ethyl]-1-((R)-1-tert-butoxycarbonylamino-2-hydroxy-ethyl)-3-oxo-dihydro-pyrrolo[1,2-c]oxazole-7a-carboxylic acid methyl ester

: 372187-37-6
(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

Guidance literature:: With chromium(VI) oxide; sulfuric acid; In acetone; at 20 ℃; for 0.666667h;
DOI:10.1021/ja016403w

Reference yield:

: 372187-29-6
(2R,5R)-2-[(1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylaminopropyl]-5-[(R)-3-(tert-butyldiphenylsilanyloxy)-2-hydroxypropyl]pyrrolidine-1,2-dicarboxylic acid, 2-benzyl ester, 1-methyl ester

: 372187-37-6
(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: triethylamine; DMAP / CH₂Cl₂ / 1 h / 0 °C

2: 619 mg / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

3: 100 percent / H₂ / PtO₂ / ethyl acetate / atmospheric pressure

4: aq. H₂SO₄; CrO₃ / acetone / 0.67 h / 20 °C

5: 472 mg / tetrahydrofuran; diethyl ether / 10 h

6: 78 percent / Mg; methanol / 2 h / 35 - 40 °C

7: sodium azide / dimethylformamide / 7 h / 20 °C

8: H₂ / Pd/C / methanol / atmospheric pressure

9: triethylamine / CH₂Cl₂ / 20 °C

10: 117 mg / aq. H₂SO₄; CrO₃ / acetone / 0.67 h / 20 °C

With chromium(VI) oxide; methanol; dmap; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; triethylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; 4: Jones oxidation / 10: Jones oxidation;
DOI:10.1021/ja016403w

Reference yield:

: (2R,5R)-5-[(R)-3-(tert-Butyl-diphenyl-silanyloxy)-2-methanesulfonyloxy-propyl]-2-((1S,2R)-1,3-diacetoxy-2-tert-butoxycarbonylamino-propyl)-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-methyl ester

: 372187-37-6
(1S,5R,7aR)-1-(S-tert-butoxycarbonylamino-carbonylmethyl)-5-[S-2-(3,5-dichloro-4-benzoxybenzoylamino)-2-methoxycarbonylethyl]-3-oxo-dihydropyrrolo[1,2-c]oxazole-7a-carboxylic acid, methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 619 mg / TBAF; AcOH / tetrahydrofuran / 1 h / 20 °C

2: 100 percent / H₂ / PtO₂ / ethyl acetate / atmospheric pressure

3: aq. H₂SO₄; CrO₃ / acetone / 0.67 h / 20 °C

4: 472 mg / tetrahydrofuran; diethyl ether / 10 h

5: 78 percent / Mg; methanol / 2 h / 35 - 40 °C

6: sodium azide / dimethylformamide / 7 h / 20 °C

7: H₂ / Pd/C / methanol / atmospheric pressure

8: triethylamine / CH₂Cl₂ / 20 °C

9: 117 mg / aq. H₂SO₄; CrO₃ / acetone / 0.67 h / 20 °C

With chromium(VI) oxide; methanol; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; hydrogen; magnesium; acetic acid; triethylamine; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; 3: Jones oxidation / 9: Jones oxidation;
DOI:10.1021/ja016403w