Hydrochloric Acid → HCID 59212055、化合物

HRID 2243984ノート

反応式

HRID 2243984 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:19][C:20]([O:22]C)=[O:21])[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C1COCC1.CO.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH2:19][C:20]([OH:22])=[O:21])[C:9](=[O:18])/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:6][CH:7]=1

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59212030{(4-Bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid, methyl ester

生成物 1

HCID 59212055HCID 59212055、化合物収率 97%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of {(4-bromophenyl)-[(E)-(3-phenylacryloyl)]amino}acetic acid, methyl ester 1 (14.61 g, 0.39 mol) in THF (150 mL) and methanol (50 mL) was treated with lithium hydroxide (2.80 g, 0.117 mol) in water (50 mL). The reaction mixture was stirred at room temperature for 45 min and then acidified with conc. hydrochloric acid and concentrated in vacuo. The residue was diluted with ethyl acetate and washed with 10% hydrochloric acid, brine, dried (Na2SO4) and the organic solution evaporated to give the title compound as a viscous oil (13.82 g, 97%). 1HNMR (300 MHz) (CDCl3) δ 4.53 (2H, s), 6.36 (1H, d, J=16 Hz), 7.27 (2H, d), 7.3-7.4 (5H, m), 7.60 (2H, d) and 7.76 (1H, d, J=16 Hz).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 10% hydrochloric acid, brine
  4. dry with materialdried (Na2SO4)
  5. customthe organic solution evaporated

出典と根拠

ORDレコード
ord-1d39399cc59d4dae85560320c3ef76ed
出典データセット
uspto-grants-2010_03
特許番号
US07678785B2

反応ノート

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