(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

Base Information

Chemical Name:(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester
CAS No.:398476-15-8
Molecular Formula:C₂₉H₃₈N₂O₉
Molecular Weight:558.629
Hs Code.:

(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

Synonyms:(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

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Chemical Property of (3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

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Technology Process of (3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

There total 5 articles about (3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic 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: 73.0%

: 398476-13-6
N-(4-methoxybenzyl)-5-amino-1-pent-2-ynoic tert-butyl ester

: 398476-14-7
(3rac, 5R)-1-(tert-butoxycarbonyl)-3-(thioethoxycarbonyl)-2-pyrrolidinon-5-carboxylic methyl ester

: 398476-15-8
(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

Guidance literature:: With silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In acetonitrile; at 20 ℃; for 14h;
DOI:10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P

Reference yield:

: 128811-48-3
1‐(tert‐butyl) 2‐methyl (R)‐5‐oxopyrrolidine‐1,2‐dicarboxylate

: 398476-15-8
(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: LiHMDS / tetrahydrofuran / 1 h / -78 °C

1.2: 95 percent / tetrahydrofuran / -78 °C

2.1: 73 percent / AgOTf; (iPr)2NEt / acetonitrile / 14 h / 20 °C

With silver trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; acetonitrile;
DOI:10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P

Reference yield:

: 146980-79-2
N-(4-methoxybenzyl)-4-amino-1-butyne

: 398476-15-8
(3rac, 5R)-1-(tert-butoxycarbonyl)-3-{[(N-tert-butoxycarbonyl)-N-(4-methoxybenzyl)but-3-yn-1-yl]carbamoyl}-2-pyrrolidinon-5-carboxylic methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 86 percent / DMAP; NEt₃ / CH₂Cl₂ / 72 h / 20 °C

2.1: nBuLi / diethyl ether; hexane / 0.5 h / -78 °C

2.2: 96 percent / diethyl ether; hexane / 1.25 h / -78 - 20 °C

3.1: 73 percent / pTsOH*H₂O / 2-methyl-propan-2-ol; diethyl ether / 16 h / 20 °C

4.1: 73 percent / AgOTf; (iPr)2NEt / acetonitrile / 14 h / 20 °C

With dmap; n-butyllithium; silver trifluoromethanesulfonate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; hexane; dichloromethane; acetonitrile; tert-butyl alcohol;
DOI:10.1002/1521-3765(20011119)7:22<4811::AID-CHEM4811>3.0.CO;2-P