(9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

Base Information

Chemical Name:(9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide
CAS No.:356548-87-3
Molecular Formula:C₂₄H₃₆N₄O₆
Molecular Weight:476.573
Hs Code.:

Synonyms:(9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

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Chemical Property of (9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

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Technology Process of (9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

There total 14 articles about (9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide 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: 35.0%

: 2687-43-6
O-benzylhydoxylamine hydrochloride

: 356548-86-2
(9S,12R,13S)-12-Isobutyl-9-methylcarbamoyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-13-carboxylic acid

: 356548-87-3
(9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

Guidance literature:: With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃;
DOI:10.1021/jm010127e

Reference yield:

: 356548-84-0
tert-butyl (9S,12R)-13-(butoxycarbonyl)-12-isobutyl-9-[(methylamino)carbonyl]-3,11-dioxo-1-phenyl-2,14-dioxa-4,10-diazahexadecan-16-oate

: 356548-87-3
(9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Pd/C / propan-2-ol / 2 h

2: HCl / dioxane / 2 h

3: BOP; DIEA / dimethylformamide; CHCl₃ / 20 °C

4: 73 percent / aq. LiOH / tetrahydrofuran / 2 h / 20 °C

5: 35 percent / BOP; DIEA / tetrahydrofuran / 20 °C

With hydrogenchloride; lithium hydroxide; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; chloroform; N,N-dimethyl-formamide; isopropyl alcohol;
DOI:10.1021/jm010127e

Reference yield:

: 113543-30-9
(S)-4-benzyl-3-(4-methylpentanoyl)oxazolidin-2-one

: 356548-87-3
(9S,12R,13S)-12-Isobutyl-3,11-dioxo-1-oxa-4,10-diaza-cyclotridecane-9,13-dicarboxylic acid 13-(benzyloxy-amide) 9-methylamide

Guidance literature:: Multi-step reaction with 11 steps

1: 1.) LDA

2: 74 percent / aq. LiOH, H₂O₂

3: 79 percent / DBU

4: 1.) NaH

5: 99 percent / H₂ / Pd-C

6: 75 percent / BOP

7: H₂ / Pd-C

8: 4N aq. HCl / dioxane

9: 50 percent / BOP

10: 73 percent / 1N aq. LiOH

11: 21 percent / BOP

With hydrogenchloride; lithium hydroxide; hydrogen; dihydrogen peroxide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; palladium on activated charcoal; In 1,4-dioxane;
DOI:10.1021/jm970849z