3-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid → 1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[3-((3RS,4SR)-3,4-dihydroxy-piperidin-1-yl)-3-oxo-propyl]-[1,4]diazepan-5-one

HRID 2095532Notes

Reaction equation

HRID 2095532 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][C:23]([OH:25])=O)[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C([Si](C)(C)[O:31][C@H:32]1[C@@H:37]([O:38][Si](C(C)(C)C)(C)C)[CH2:36][CH2:35][NH:34][CH2:33]1)(C)(C)C>>[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][C:23]([N:34]3[CH2:35][CH2:36][CH:37]([OH:38])[CH:32]([OH:31])[CH2:33]3)=[O:25])[CH2:15][CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

3

Reactant 2

HCID 670745383-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid2×HCID 131727826(cis)-(Rac)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-piperidine2×

Product 1

HCID 895681481-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[3-((3RS,4SR)-3,4-dihydroxy-piperidin-1-yl)-3-oxo-propyl]-[1,4]diazepan-5-oneYield 95%

Procedure

In analogy to the procedure described in Example 1,3-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-propionic acid (intermediate 5) and (cis)-(rac)-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-piperidine (intermediate 9) gave the titled compound in 95% yield as a white solid. MS: 712.5 (MH+, 2Cl).

Sources & evidence

ORD record
ord-d806f45733a64896a09020ae61455881
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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