(3R,4R)-3,4-bis((tert-butyl(dimethyl)silyl)oxy)piperidine → 4-{4-[(3RS,4SR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-butyl}-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

HRID 1867432Notes

Reaction equation

HRID 1867432 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])[N:16]([CH2:21][CH2:22][CH2:23][CH2:24]I)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:26]([Si:30]([CH3:47])([CH3:46])[O:31][C@H:32]1[C@H:37]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:36][CH2:35][NH:34][CH2:33]1)([CH3:29])([CH3:28])[CH3:27]>>[C:26]([Si:30]([CH3:47])([CH3:46])[O:31][CH:32]1[CH:37]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[CH2:36][CH2:35][N:34]([CH2:24][CH2:23][CH2:22][CH2:21][N:16]2[C:17](=[O:20])[CH2:18][CH2:19][N:13]([C:11](=[O:12])/[CH:10]=[CH:9]/[C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)[CH2:14][CH2:15]2)[CH2:33]1)([CH3:29])([CH3:28])[CH3:27]

Participants

3

Reactant 2

HCID 10893352(3R,4R)-3,4-bis((tert-butyl(dimethyl)silyl)oxy)piperidine2×HCID 684330161-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(4-iodo-butyl)-[1,4]diazepan-5-one

Product 1

HCID 684323104-{4-[(3RS,4SR)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidin-1-yl]-butyl}-1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-[1,4]diazepan-5-one

Procedure

In analogy to the procedure described in example 163A, 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(4-iodo-butyl)-[1,4]diazepan-5-one (example 9B) and (trans)-(rac)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-piperidine (intermediate 26) gave the title compound as colorless oil.

Sources & evidence

ORD record
ord-ffc88ba9ad0b44b18172864912a4b4e6
Source dataset
uspto-grants-2009_12
Patent number
US07632829B2

Reaction notes

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