7-Hydroxyflavone → (2S)-2-Methoxy-3-{4-[5-(4-oxo-2-phenyl-4H-chromen-7-yloxy)-pent-1-ynyl]-phenyl}-propionic acid

HRID 459095

Reaction equation

C([O:3][C:4](=[O:21])[CH:5]([O:19][CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17]Br)=[CH:9][CH:8]=1)C.[OH:22][C:23]1[CH:32]=[C:31]2[C:26]([C:27](=[O:39])[CH:28]=[C:29]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[O:30]2)=[CH:25][CH:24]=1>>[CH3:20][O:19][C@@H:5]([CH2:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][CH2:17][O:22][C:23]2[CH:32]=[C:31]3[C:26]([C:27](=[O:39])[CH:28]=[C:29]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[O:30]3)=[CH:25][CH:24]=2)=[CH:11][CH:12]=1)[C:4]([OH:3])=[O:21]

Participants

Reactant 2

HCID 52818947-Hydroxyflavone

HCID 694219733-[4-(5-Bromo-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester

Product 1

HCID 69424192(2S)-2-Methoxy-3-{4-[5-(4-oxo-2-phenyl-4H-chromen-7-yloxy)-pent-1-ynyl]-phenyl}-propionic acid

Procedure

The title compound was prepared from 3-[4-(5-Bromo-pent-1-ynyl)-phenyl]-2-methoxy-propionic acid ethyl ester from Example 24, Step A and 7-hydroxyflavone in a manner analogous to that described for Example 24, Step B. MS(ES) for C30H26O6[M+H]+:483.2.

Sources & evidence

ORD record: ord-a475a4d160834725828f465f2d741a74
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07192982B2

Linked notes

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