Triethylamine → HCID 86605382、化合物

HRID 1180442ノート

反応式

HRID 1180442 の反応式
[C:1]([OH:9])(=O)[C@H:2]([CH2:4][CH:5]([CH3:7])[CH3:6])[OH:3].Cl.[NH2:11][CH2:12][C:13]#[N:14].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C.CCOC(C)=O.CCCCCC>[C:12]([CH2:13][NH:14][C:1](=[O:9])[C@@H:2]([OH:3])[CH2:4][CH:5]([CH3:6])[CH3:7])#[N:11]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 83697Leucic acid, L-HCID 516892Sodium BicarbonateHCID 11491918Aminoacetonitrile hydrochloride

生成物 1

HCID 86605382HCID 86605382、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

L-leucic acid (85 g, 0.643 mole), amino acetonitrile hydrochloride (68 g, 0.734 mole, 1.14 eg), pyBOP (319 g, 0.612 mole, 0.95 eg) were mixed together in DMF (1 L) and cooled at 0° C. Triethylamine (149 g, 1.47 mole, 2.4 eg) was added dropwise at a rate to maintain internal temperature ≦20° C. Reaction mixture was then allowed to warm to room temperature and stirred for 18 hours. Reaction mixture was poured portionwise into saturated NaHCO3 (4 L) and extracted with EtOAc (2×1 L). Half saturated NaCl solution was added to help partition. Combined organic fractions were washed with brine, 0.5 N HCl, brine, dried and evaporated to give a dark red oil. The latter was passed through a silica plug with 50% EtOAc/hexane to give of the title compound.

後処理

  1. temperatureto maintain internal temperature ≦20° C
  2. customReaction mixture
  3. temperatureto warm to room temperature
  4. customReaction mixture
  5. extractionextracted with EtOAc (2×1 L)
  6. additionHalf saturated NaCl solution was added
  7. customto help partition
  8. washCombined organic fractions were washed with brine, 0.5 N HCl, brine
  9. customdried
  10. customevaporated
  11. customto give a dark red oil

出典と根拠

ORDレコード
ord-45c0a8ce5ce0442d91c2be7ad1a2d3cb
出典データセット
uspto-grants-2007_10
特許番号
US07279478B2

反応ノート

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