methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

Base Information

Chemical Name:methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates
CAS No.:120632-45-3
Molecular Formula:C₂₃H₃₂ClNO₄S
Molecular Weight:454.03
Hs Code.:

Synonyms:methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

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Chemical Property of methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

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Technology Process of methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

There total 11 articles about methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates 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: 93.9%

: 2888-06-4
3-chlorophenylsulfonyl chloride

: 197069-37-7
(1R,2R,3S,5S)-(5Z)-7-(2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)-hept-5-enoic acid methyl ester

: 120632-45-3
methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

Guidance literature:: With triethylamine; In dichloromethane; for 1h; Ambient temperature;
DOI:10.1248/cpb.37.1524

Reference yield:

: 17814-85-6
(4-carboxybutyl)triphenylphosphonium bromide

: 120632-45-3
methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) 60percent sodium hydride / 1.) DMSO, room temperature, 2.) ether, 10 min,

2: 93.4 percent / K₂Cr₂O₇, H₂SO₄ / acetone / 1 h / 0 °C

3: 1.) ethyl chloroformate, 2.) sodium azide / 1.) acetone, 0 deg C, 1 h, 2.) acetone, water, 0 deg C, 1 h,

4: benzene / 0.5 h / Heating

5: 72 h / Heating

6: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

7: 93.9 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With potassium dichromate; sodium azide; sulfuric acid; chloroformic acid ethyl ester; sodium hydride; triethylamine; trifluoroacetic acid; In dichloromethane; acetone; benzene;
DOI:10.1248/cpb.37.1524

Reference yield:

: 126264-15-1
[(1R,2R,3R,5S)-6,6-Dimethyl-3-(2-oxo-ethyl)-bicyclo[3.1.1]hept-2-yl]-carbamic acid tert-butyl ester

: 120632-45-3
methyl (5Z)-7-((1R,2R,3S,5S)-2-(m-chlorophenyl sulfonylamino)-6,6-dimethylbicyclo<3.1.1>hept-3-yl)hept-5-enoates

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, 0 deg C, 1 h,

2: diethyl ether / 0.17 h

3: trifluoroacetic acid / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 93.9 percent / triethylamine / CH₂Cl₂ / 1 h / Ambient temperature

With potassium tert-butylate; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane;
DOI:10.1248/cpb.37.1524