Acetic Acid → Methyl alpha-(phenylmethylamino)-3-indoleacetate

HRID 5615

反応式

HRID 5615 の反応式
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=O.[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20]1>CO>[C:2]1([CH2:1][NH:8][CH:14]([C:21]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:19][CH:20]=2)[C:13]([O:17][CH3:18])=[O:16])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 798IndoleHCID 7504BenzylamineHCID 70205Acetic acid, 2-oxo-, methyl ester

生成物 1

HCID 19796635Methyl alpha-(phenylmethylamino)-3-indoleacetate収率 86.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a stirred solution of 6.43 g (0.06 mole) of benzylamine and 5 mL (5.25 g, 0.09 mole) of acetic acid in 50 mL of MeOH was added a solution of 5.28 g (0.06 mole) of methyl glyoxylate in 50 mL of MeOH followed by 5.86 g (0.05 mole) of indole. The resulting solution was allowed to stand for 69 hours. The solvent was evaporated. The residue was treated with 200 mL of H2O. Sodium bicarbonate was added until CO2 evolution ceased. The mixture was extracted with CH2Cl2 (3×100 mL). The combined extracts were washed with 50 mL brine and dried over MgSO4. Evaporation of the solvent left 16.2 g of orange-brown oil which solidified upon standing. The solid was chromatographed on a 700 g column of silica gel. The column was eluted with 7.5% MeOH-CH2Cl2 and 200 mL fractions were collected. The fractions were assayed by silica gel (TLC (1×4") (5% MeOH-CH2Cl2). Fractions 10-14 were combined giving 12.7 g of red oil. The oil was chromatographed on a 700 g column of silica gel. The column was eluted with 40% acetone-Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel TLC (1×4") (40% acetone-Skellysolve B). Fractions 11-14 were combined and crystallized from ether-THF-hexane giving 8.07 g (55%) of the title compound as a pale pink solid, m.p. 91.5°-93° C.

後処理

  1. customThe solvent was evaporated
  2. additionThe residue was treated with 200 mL of H2O
  3. additionSodium bicarbonate was added until CO2 evolution
  4. extractionThe mixture was extracted with CH2Cl2 (3×100 mL)
  5. washThe combined extracts were washed with 50 mL brine
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent
  8. waitleft 16.2 g of orange-brown oil which
  9. customThe solid was chromatographed on a 700 g column of silica gel
  10. washThe column was eluted with 7.5% MeOH-CH2Cl2 and 200 mL fractions
  11. customwere collected

出典と根拠

ORDレコード
ord-69d35a3bb1bc42339ef1b49a84e23b5f
出典データセット
uspto-grants-1993_09
特許番号
US05245046

関連ノート

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