6-Methoxy(2-naphthyl]propanoate → HCID 178487476、化合物

HRID 386951

反応式

HRID 386951 の反応式
[CH2:1]1[CH2:6][C@H:5]([C:7]([OH:9])=[O:8])[CH2:4][CH2:3][C@H:2]1[CH2:10][NH2:11].[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([CH:24]([CH3:28])[C:25]([O-:27])=[O:26])[CH:18]=[CH:17]2.[CH3:29][C:30]([O:33][CH3:34])(C)C.CC(C)=[O:37].O>>[CH3:12][O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[CH:20]=[C:19]([C@H:24]([CH3:28])[C:25]([O:27][CH2:29][CH2:30][O:33][C:34]([NH:11][CH2:10][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:7]([OH:9])=[O:8])[CH2:6][CH2:1]1)=[O:37])=[O:26])[CH:18]=[CH:17]2

参加物

4

反応物 3

HCID 46366026-Methoxy(2-naphthyl]propanoateHCID 86610273MTBE acetone waterHCID 178511262HCID 178511262、化合物

生成物 1

HCID 178487476HCID 178487476、化合物収率 9%

実験手順

Following the general nucleophilic carbamoylation procedure, tranexamic acid (6.9 g, 43.9 mmol) and 1-[(2,5-dioxopyrrolidinyl)oxycarbonyloxy]ethyl (2S)-2-[6-methoxy(2-naphthyl]propanoate (ca. 6.2 g, 14.9 mmol) were reacted in the MTBE/acetone/water mixture (160 mL) to yield the title compound 27 (579 mg, 9% yield) as a colorless powder after work-up, purification by silica gel column chromatography using ethyl acetate/hexane mixtures from 2:1 to 4:1 as eluent, and subsequent mass-guided preparative HPLC. 1NMR (400 MHz, DMSO-d6): δ=0.76-0.94 (m, 2H), 1.10-1.92 (m, 13H), 1.98-2.14 (m, 1H), 2.66-2.86 (m, 2H), 3.82-3.95 (m, 4H), 6.64-6.76 (m, 1H), 7.10-7.17 (m, 1H), 7.24-7.50 (m, 3H), 7.63-7.80 (m, 3H), 11.99 (br.s, 1H). MS (PSI) m/z 480.16 (M+Na)+; 456.18 M−H)−.

出典と根拠

ORDレコード
ord-e8393fed670246bab942003e21b1ea30
出典データセット
uspto-grants-2013_02
特許番号
US08372881B2

関連ノート

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