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Methanol → 3-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid

HRID 650423
ノート
印刷プレビュー

反応式

HRID 650423 の反応式
[C:1]([CH2:4][O:5][C:6]1[C:11](OC)=[CH:10][CH:9]=[CH:8][C:7]=1[CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[CH:21]=2)[CH:16]([C:27]2[CH:32]=[CH:31][C:30]3[O:33][CH2:34][O:35][C:29]=3[CH:28]=2)[CH:15]1[CH2:36][C:37]([OH:39])=[O:38])([OH:3])=[O:2].C1C2C(=CC=CC=2)CC1.[OH-:49].[Na+].O.[CH3:52]O>>[C:1]([CH2:4][O:5][C:6]1[CH:11]=[C:10]([O:49][CH3:52])[CH:9]=[CH:8][C:7]=1[CH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH2:24][CH2:25][CH3:26])[CH:21]=2)[CH:16]([C:27]2[CH:32]=[CH:31][C:30]3[O:33][CH2:34][O:35][C:29]=3[CH:28]=2)[CH:15]1[CH2:36][C:37]([OH:39])=[O:38])([OH:3])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 887MethanolHCID 962WaterHCID 10326IndaneHCID 14798Sodium HydroxideHCID 70232555(1RS,2SR,3RS)-3-(2-Carboxymethoxy-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid

生成物 1

HCID 101663713-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid
収率 90%

反応条件

温度
70 °C

実験手順

(1RS,2SR,3RS)-3-(2-Carboxymethoxy-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid. To a solution of 1RS,2RS,3RS)-3-(2-carboxymethoxy-4-methoxyphenyl)-2-cyanomethyl-1-(3,4-methylenedioxyphenyl)-5-prop-1-yloxy)indane (290 mg, 0.56 mmol) in methanol (ca. 1 ml) was added aqueous 2 N NaOH solution (0.3 ml) followed by H2O (8 ml) then (with caution) Na2O2 (120 mg). The mixture was heated to 70° C. and stirred for 20 h at which time HPLC showed only 15% hydrolysis. The mixture was stirred at 85° C. for 3 days with 3 (100 mg) portions of Na22 added each day. the reaction mixture was partitioned between EtOAc and 3N HCl. The organic extract was washed with H2O then brine, dried (Na2SO4) and solvent removed in vacuo to afford the product as an oil (228 mg, 90% pure by HPLC) Final purification was obtained by crystallization as the bis cyclohexylamine salt. mp 210-212° C.

後処理

  1. custom15% hydrolysis
  2. additionadded each day
  3. customthe reaction mixture was partitioned between EtOAc and 3N HCl
  4. extractionThe organic extract
  5. washwas washed with H2O
  6. dry with materialbrine, dried (Na2SO4) and solvent
  7. customremoved in vacuo

出典と根拠

ORDレコード
ord-d346557894a94b978056e3adf9f3385d
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06271399B1

反応ノート

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