Dicyclohexylcarbodiimide → Pent-4-ynoic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

HRID 1425669

반응식

HRID 1425669 반응식
[C:1]([OH:7])(=[O:6])[C:2]#[C:3][CH2:4][CH3:5].C1(N=C=NC2CCCCC2)CCCCC1.O[N:24]1[C:29](=[O:30])[C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]=2[N:26]=[N:25]1>C1COCC1>[O:30]=[C:29]1[N:24]([O:6][C:1](=[O:7])[CH2:2][CH2:3][C:4]#[CH:5])[N:25]=[N:26][C:27]2[CH:34]=[CH:33][CH:32]=[CH:31][C:28]1=2

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-one2회HCID 3243792-Pentynoic acid

생성물 1

HCID 59336624Pent-4-ynoic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-10 °C

실험 절차

Pentynoic acid (200 mg, 2.04 mmol) was dissolved in THF (4 mL). The solution was cooled in a brine-icewater bath. A solution of dicyclohexylcarbodiimide (421 mg, 2.04 mmol) in THF (2 mL) was added. 3-Hydroxy-1,2,3-benzotriazin-4(3H)-one (333 mg, 2.04 mmol) was added after 5 minutes. The reaction mixture was stirred 1 h at −10° C. and then 2 h at room temperature. TLC indicated full conversion of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (eluent: ethyl acetate). Precipitated salts were filtered off. The filtrate was concentrated in vacuo and crystallized from hexane (4 mL). The crystals were filtered off and dried. Yield: 450 mg, 93%. RF=0.8 (ethyl acetate).

후처리

  1. temperatureThe solution was cooled in a brine-icewater bath
  2. custom2 h
  3. customat room temperature
  4. filtrationPrecipitated salts were filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customcrystallized from hexane (4 mL)
  7. filtrationThe crystals were filtered off
  8. customdried

출처 및 근거

ORD 기록
ord-b4512c63238b41e6808a75cbeb137263
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08932992B2

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