2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

Base Information

Chemical Name:2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester
CAS No.:145072-02-2
Molecular Formula:C₂₅H₃₀N₂O₄
Molecular Weight:422.524
Hs Code.:

Synonyms:2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

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Chemical Property of 2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

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Technology Process of 2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

There total 8 articles about 2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-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: 87.0%

: 122181-86-6
1-carbomethoxy-2-amino-4,5,6,7-tetrahydro-2H-isoindole

: 145071-98-3
(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoic acid

: 145072-02-2
2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; for 72h; Ambient temperature;
DOI:10.1021/jo970288j

Reference yield:

: 81445-44-5
(S)-2-(benzyloxy)propanal

: 145072-02-2
2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1) THF, hexane, -78 deg C, 45 min, -78 deg C --> rt, 2-4 h, rt, 8 h

2: 1.) octacarbonyldicobalt, 2.) Bu₂BOTf, diisopropylethylamine, 3.) ceric ammonium nitrate / 1) Et₂O, 40 min; 2) CH₂Cl₂, -78 deg C, 30 min, 0 deg C, 30 min; 3) acetone, rt, 40 min

3: 81 percent / aq. LiOH, aq. H₂O₂ / tetrahydrofuran / 1) 0 deg C, 1 h; 2) rt, 2 h

4: 87 percent / EDCI / tetrahydrofuran / 72 h / Ambient temperature

With lithium hydroxide; n-butyllithium; dicobalt octacarbonyl; ammonium cerium(IV) nitrate; di-n-butylboryl trifluoromethanesulfonate; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1021/jo970288j

Reference yield:

: 15753-50-1,25712-33-8
cis-1,2-cyclohexanedimethanol

: 145072-02-2
2-[(2R,3R)-3-((S)-1-Benzyloxy-ethyl)-2-methyl-pent-4-ynoylamino]-4,5,6,7-tetrahydro-2H-isoindole-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, DMSO, 2.) NEt₃ / 1) CH₂Cl₂, -78 deg C, 3 h 20 min; 2) CH₂Cl₂, rt, 15 h

2: 81 percent / aq. HCl / tetrahydrofuran / 40 °C

3: 1.) AlCl₃ / 1) 1,2-dichloroethane, CH₂Cl₂, rt, 8 d; 2) reflux, 1 h

4: 76 percent / hydrazine monohydrate / ethanol / 2 h / Ambient temperature

5: 87 percent / EDCI / tetrahydrofuran / 72 h / Ambient temperature

With hydrogenchloride; aluminium trichloride; oxalyl dichloride; hydrazine hydrate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; ethanol;
DOI:10.1021/jo970288j