3-Hydroxy-N-phenylaniline → (2s)-2-Methoxy-3-{4-[3-(3-phenylamino-phenoxy)-propoxy]-phenyl}-propionic acid

HRID 459121

反応式

HRID 459121 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C@H:13]([O:17][CH3:18])[C:14]([OH:16])=[O:15])=[CH:8][CH:7]=1.[CH:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28](O)[CH:27]=2)=[CH:21][CH:20]=1>>[CH3:18][O:17][C@@H:13]([CH2:12][C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH2:3][CH2:2][O:1][C:30]2[CH:29]=[CH:28][CH:27]=[C:26]([NH:25][C:22]3[CH:23]=[CH:24][CH:19]=[CH:20][CH:21]=3)[CH:31]=2)=[CH:7][CH:8]=1)[C:14]([OH:16])=[O:15]

参加物

3

反応物 2

HCID 75463-Hydroxy-N-phenylanilineHCID 69424952(2S)-3-[4-(3-Hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid

生成物 1

HCID 58822777(2s)-2-Methoxy-3-{4-[3-(3-phenylamino-phenoxy)-propoxy]-phenyl}-propionic acid

実験手順

The title compound was prepared from (2S)-3-[4-(3-hydroxy-propoxy)-phenyl]-2-methoxy-propionic acid linked to Wang's Resin (Example 94, Step D) via Mitsunobu coupling with 3-hydroxydiphenylamine and cleavage from the resin (Standard Procedure G) gave an oily solid (4%). 1H-NMR (200.15 MHz, CDCl3): δ 7.31–6.81 (m, 8H), 6.83 (d, 2H, J=8.6), 6.65–6.62 (m, 2H), 6.48 (dd, 1H, J=8.2, 2.1), 4.12 (t, 4H, J=6.2), 3.99 (dd, 1H, J=7.0, 4.4), 3.40 (s, 3H), 3.10 (dd, 1H, J=14.2, 4.4), 2.95 (dd, 1H, J=14.2, 7.0), 2.22 (qn, 2H, J=6.2).

出典と根拠

ORDレコード
ord-a54321e201dd471eb877468b80ba8c50
出典データセット
uspto-grants-2007_03
特許番号
US07192982B2

関連ノート

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