Ethyl isocyanatoacetate → HCID 24830240、化合物

HRID 2410045ノート

反応式

HRID 2410045 の反応式
[CH3:1][CH:2]([CH3:19])[CH2:3][CH2:4][N:5]1[C:10](=[O:11])[CH2:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:6]1=[O:18].C(N(C(C)C)CC)(C)C.[N:29]([CH2:32][C:33]([O:35]CC)=[O:34])=[C:30]=[O:31]>ClCCl>[OH:11][C:10]1[N:5]([CH2:4][CH2:3][CH:2]([CH3:19])[CH3:1])[C:6](=[O:18])[N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[C:8](=[O:12])[C:9]=1[C:30]([NH:29][CH2:32][C:33]([OH:35])=[O:34])=[O:31]

参加物

5

反応物 3

HCID 76283Ethyl isocyanatoacetateHCID 81531DiisopropylethylamineHCID 18375361HCID 18375361、化合物

生成物 1

HCID 24830240HCID 24830240、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

-{[6-Hydroxy-1,3-bis(3-methylbutyl)-2,4-dioxo-1,2,3,4-tetrahydro-5-pyrimidinyl]carbonyl}glycine. A mixture of 1,3-bis(3-methylbutyl)-2,4,6(1H,3H,5H)-pyrimidinetrione (1.2 g, 4.47 mmoles) and diisopropylethylamine (1.56 mL, 8.94 mmoles) was stirred in dichloromethane (30 mL) and treated with ethyl isocyanatoacetate (501 uL, 4.47 mmoles). The mixture was stirred for 5 hours, washed with 1 molar hydrochloric acid (×2), evaporated, taken up in ethanol-6 molar sodium hydroxide and stirred overnight. The mixture was acidified and extracted into ethyl acetate (×2). The extracts were washed with 1 molar hydrochloric acid evaporated, dried and evaporated. The title compound was recrystallized from acetic acid (430 mg, 26%). 1H NMR (400 MHz, DMSO-d6) δ ppm 13.09 (br. s, 1 H), 10.11 (s, 1 H), 4.09-4.16 (m, 2 H), 3.77-3.86 (m, 4 H), 1.51-1.62 (dt, J=13.29, 6.59, 6.59, 6.59, 6.59 Hz, 2 H), 1.42 (q, J=7.07 Hz, 4 H), 0.91 (d, J=6.57 Hz, 12 H).

後処理

  1. washwashed with 1 molar hydrochloric acid (×2)
  2. customevaporated
  3. stirringstirred overnight
  4. extractionextracted into ethyl acetate (×2)
  5. washThe extracts were washed with 1 molar hydrochloric acid
  6. customevaporated
  7. customdried
  8. customevaporated
  9. customThe title compound was recrystallized from acetic acid (430 mg, 26%)

出典と根拠

ORDレコード
ord-6e7e951143ab4f6aae06267469ccbb34
出典データセット
uspto-grants-2014_08
特許番号
US08815884B2

反応ノート

読み込み中…