(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-one → (S)-tert-butyl 3-(acetylthiomethyl)-4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazine-1-carboxylate

HRID 1502046Notes

Reaction equation

HRID 1502046 reaction equation
[C:1]([S:4][CH2:5][C@H:6]1[N:11]([CH2:12][C@H:13]([OH:25])[C:14]2[C:15]([CH3:24])=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19](=[O:23])[O:18][CH2:17]3)[CH2:10][CH2:9][N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:7]1)(=[O:3])[CH3:2].CC1C2COC(=O)C=2C=CC=1[C@H]1CO1>>[C:1]([S:4][CH2:5][C@H:6]1[N:11]([CH2:12][C@@H:13]([OH:25])[C:14]2[C:15]([CH3:24])=[C:16]3[C:20](=[CH:21][CH:22]=2)[C:19](=[O:23])[O:18][CH2:17]3)[CH2:10][CH2:9][N:8]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:7]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 59568665(S)-4-methyl-5-(oxiran-2-yl)isobenzofuran-1(3H)-oneHCID 86727079(S)-tert-butyl 3-(acetylthiomethyl)-4-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazine-1-carboxylate

Product 1

HCID 117690268(S)-tert-butyl 3-(acetylthiomethyl)-4-((S)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazine-1-carboxylate

Procedure

Synthesis is analogous to that for (S)-tert-butyl 3-(acetylthiomethyl)-4-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)piperazine-1-carboxylate starting from 4-methyl-5-[(2S)-oxiran-2-yl]-2-benzofuran-1(3H)-one: LC/MS: [(M+1)]+=465.3;

Workup

  1. customSynthesis

Sources & evidence

ORD record
ord-2411ced2f76a49a190048c21896a122d
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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