4-Formylbenzoic acid → 4-[(2-tert-Butoxycarbonylethylamino)methyl]benzoic acid

HRID 444976

反応式

HRID 444976 の反応式
Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].C(N(C(C)C)CC)(C)C.[C:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)([OH:23])=[O:22].C([BH3-])#N.[Na+]>CO.O.C(O)(=O)C>[C:8]([O:7][C:5]([CH2:4][CH2:3][NH:2][CH2:28][C:27]1[CH:30]=[CH:31][C:24]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1)=[O:6])([CH3:11])([CH3:10])[CH3:9]

参加物

8

反応物 4

HCID 120884-Formylbenzoic acidHCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 16218890Tert-butyl 3-aminopropanoate hydrochloride

生成物 1

HCID 596879094-[(2-tert-Butoxycarbonylethylamino)methyl]benzoic acid

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Tert-butyl 3-aminopropanoate hydrochloride (5 g, 27.7 mmol) was dissolved in methanol (150 mL). Diisopropylethylamin (4.73 mL, 27.7 mmol) was added followed by 4-carboxybenzaldehyd. The mixture is heated to reflux for 1 hour. After cooling to room temperature sodium cyanoborohydride (1.77 g, 22.1 mmol) was added under nitrogen and stirred for 1 hour at room temperature. Acetic acid (15 mL) was added and the mixture was stirred for an additional 1 hour. The mixture was poured into water (300 mL) and stirred at room temperature over night. The water solution was washed with ethyl acetate (3×250 mL). The organic phase dried (Na2SO4) and solvent removed in vacuo to yield the crude product as an oil which solidifies by standing. The crude product was used in the next step without further purification.

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 1 hour
  3. additionwas added under nitrogen
  4. stirringthe mixture was stirred for an additional 1 hour
  5. stirringstirred at room temperature over night
  6. washThe water solution was washed with ethyl acetate (3×250 mL)
  7. dry with materialThe organic phase dried (Na2SO4) and solvent
  8. customremoved in vacuo

出典と根拠

ORDレコード
ord-529bb2850dd94b4484bee76555c5f515
出典データセット
uspto-grants-2013_07
特許番号
US08476228B2

関連ノート

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