Acetic Acid → 3-Pentylamino-phthalic acid dimethyl ester

HRID 9995

反応式

HRID 9995 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7].[CH:16](=O)[CH2:17][CH2:18][CH2:19][CH3:20].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:15])[C:4]1[C:5](=[C:10]([NH:14][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:11]=[CH:12][CH:13]=1)[C:6]([O:8][CH3:9])=[O:7]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8063PentanalHCID 5049666Sodium triacetoxyborohydrideHCID 13399384Dimethyl 3-aminobenzene-1,2-dicarboxylate

生成物 1

HCID 210401313-Pentylamino-phthalic acid dimethyl ester収率 100%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred solution of 3-amino-phthalic acid dimethyl ester (3.14 g, 15 mmol) in methylene chloride (50 ml) under a nitrogen atmosphere were added valeraldehyde (2.0 ml, 18.75 mmol) and acetic acid (5.18 ml, 90 mmol). The mixture was stirred for 5 minutes followed by addition of sodium triacetoxyborohydride (6.36 g, 30 mmol). The reaction was stirred for 30 minutes, diluted with methylene chloride (50 ml), washed with water (2×100 ml), saturated aqueous sodium bicarbonate (2×100 ml), brine (100 ml), and dried (MgSO4). The solvent was evaporated in vacuo to give 4.19 g of product (100%) that used without further purification. 1H NMR (DMSO-d6) d 7.31 (t, J=7.9 Hz, 1H), 6.81–6.75 (m, 2H), 3.85 (s, 3H), 3.82 (s, 3H), 3.15 (bs, 2H), 1.68–1.60 (m, 2H), 1.45–1.32 (m, 4H), 0.89 (t, J=6.9 Hz, 3H).

後処理

  1. stirringThe reaction was stirred for 30 minutes
  2. washwashed with water (2×100 ml), saturated aqueous sodium bicarbonate (2×100 ml), brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was evaporated in vacuo

出典と根拠

ORDレコード
ord-438d6a99b9ef41de83c883a76ce3a643
出典データセット
uspto-grants-2006_08
特許番号
US07091353B2

関連ノート

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