Tris(hydroxymethyl)aminomethane → HCID 12043808, 화합물

HRID 1282021노트

반응식

HRID 1282021 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 12043808HCID 12043808, 화합물수율 70%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-abb4b32e56e847f086e76a7364723d08
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455559B1

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