methanesulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester → 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-((S)-3,4-dihydroxy-butyl)-[1,4]diazepan-5-one

HRID 1867449Notes

Reaction equation

HRID 1867449 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[NH:16][CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].CC1(C)[O:26][C@@H:25]([CH2:27][CH2:28]OS(C)(=O)=O)[CH2:24][O:23]1>>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:9]=[CH:10]/[C:11]([N:13]2[CH2:19][CH2:18][C:17](=[O:20])[N:16]([CH2:28][CH2:27][C@H:25]([OH:26])[CH2:24][OH:23])[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 13194537methanesulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl esterHCID 620449211-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one2×

Product 1

HCID 684341311-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-((S)-3,4-dihydroxy-butyl)-[1,4]diazepan-5-one

Procedure

In analogy to the procedure described for example 167A and 167B, 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one (intermediate 1A]) and methanesulfonic acid 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethyl ester (prepared from 2-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-ethanol and methanesulfonyl chloride) gave the title compound as an white foam. MS: 401.3 (MH+, 2Cl).

Sources & evidence

ORD record
ord-de19dbda6a7a41cbbd204cb5fc3ee865
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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