Tris(hydroxymethyl)aminomethane → HCID 12043808、化合物

HRID 1282021ノート

反応式

HRID 1282021 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([CH3:19])[C:16]([OH:18])=O)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[C:24]([O:28][C:29]([N:31]1[C:35]([NH2:36])=[CH:34][C:33]([CH:37]2[CH2:39][CH2:38]2)=[N:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25].C(O)C(N)(CO)CO>O1CCCC1.C(N(CC)CC)C>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([CH3:19])[C:16]([NH:36][C:35]2[N:31]([C:29]([O:28][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:30])[N:32]=[C:33]([CH:37]3[CH2:39][CH2:38]3)[CH:34]=2)=[O:18])=[CH:13][CH:14]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

7

反応物 4

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 24386Thionyl ChlorideHCID 3780288HCID 3780288、化合物HCID 113565135-Amino-3-cyclopropyl-1H-pyrazole-1-carboxylic acid 1,1-dimethylethyl ester

生成物 1

HCID 12043808HCID 12043808、化合物収率 70%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

265 mg (1 mmol) of 2-{4-[(tert-butoxycarbonyl)amino]phenyl}propanoic acid were treated at 4° C. under nitrogen with 146 μl (2 mmol) of thionylchloride. The reaction mixture was stirred for 2.5 hours and the temperature was gradually raised to room temperature. The mixture was taken up with tetrahydrofuran and evaporated thoroughly. The resulting acyl chloride, without any further purification, was dissolved in 3 ml of dry tetrahydrofuran and added dropwise to a solution of 178 mg (0.8 mmol) of tert-butyl-5-amino-3-cyclopropyl-1H-pyrazole-1-carboxylate in 3 ml of tetrahydrofuran. 312 mg (1 mmol, loading 3.2 mmol/g) of polymer supported triethylamine were then added under stirring. After 2.5 hours 80 mg (loading 3.2 mmol/g) of polymer supported trisamine were finally added in order to quench the excess of acyl chloride. After 2 hours, the resins were filtered and washed with methanol and dichloromethane. Evaporation of the filtrate afforded 263 mg of the title compound as a foam (70% yield).

後処理

  1. customevaporated thoroughly
  2. customThe resulting acyl chloride, without any further purification
  3. dissolutionwas dissolved in 3 ml of dry tetrahydrofuran
  4. additionwere then added
  5. stirringunder stirring
  6. waitAfter 2.5 hours 80 mg (loading 3.2 mmol/g) of polymer supported
  7. customto quench the excess of acyl chloride
  8. waitAfter 2 hours
  9. filtrationthe resins were filtered
  10. washwashed with methanol and dichloromethane
  11. customEvaporation of the filtrate

出典と根拠

ORDレコード
ord-abb4b32e56e847f086e76a7364723d08
出典データセット
uspto-grants-2002_09
特許番号
US06455559B1

反応ノート

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