Citric Acid → 3-(aminomethyl)benzoic acid

HRID 1417887ノート

反応式

HRID 1417887 の反応式
Cl.CCN([CH:8]([CH3:10])[CH3:9])C(C)C.[NH:11](C(OC(C)(C)C)=O)[C@H](C(ON1C(=O)CCC1=O)=O)CC(=O)OCC1C=CC=CC=1.[C:41](O)(=O)[CH2:42][C:43]([CH2:48][C:49]([OH:51])=[O:50])(C(O)=O)O>CN(C=O)C.[Au]>[NH2:11][CH2:41][C:42]1[CH:43]=[C:48]([CH:10]=[CH:8][CH:9]=1)[C:49]([OH:51])=[O:50]

参加物

7

反応物 4

HCID 311Citric AcidHCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 135177984-Benzyl 1-(2,5-dioxopyrrolidin-1-yl) N-(tert-butoxycarbonyl)-L-aspartate

生成物 1

HCID 5060733-(aminomethyl)benzoic acid収率 92%

試薬・触媒・溶媒 2

HCID 23985Gold触媒HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
5 °C

実験手順

HCl (Mamb; 13.08 g, 70.0 mmol) was dissolved in 120 ml DMF and DIEA (24.32 ml, 140 mmol) was added, changing the pH from 4 to 7.5. The white suspension was stirred for 30 min at room temperature before a solution of Boc-Asp(OBzl)-OSu (29.40 g, 70.0 mmol) in DMF (50 ml) was added. The mixture was allowed to stir 24 hr, during which time it turned to a gold solution. The solution was added to 5% citric acid (2000 ml) and cooled to 5° C. for 3 hr. The solids were then collected by filtration, washed with ice cold water (200 ml) and ice cold ethyl ether (100 ml), and dried under reduced pressure to give the title compound as a colorless solid (29.62 g, 92%); MP=149°-151° C.; DCI-MS: [M+NH4 ]=474.

後処理

  1. additionwas added
  2. filtrationThe solids were then collected by filtration
  3. washwashed with ice cold water (200 ml) and ice cold ethyl ether (100 ml)
  4. customdried under reduced pressure

出典と根拠

ORDレコード
ord-8a26820398594c0497459aa4666308a9
出典データセット
uspto-grants-1999_03
特許番号
US05879657

反応ノート

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