Dicyclohexylcarbodiimide → N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester

HRID 528674

반응식

HRID 528674 반응식
[C:1]([NH:8][CH2:9][C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[C:4]([O:3][C:1]([NH:8][CH2:9][C:10]([O:12][N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20])=[O:11])=[O:2])([CH3:6])([CH3:7])[CH3:5]

참가 물질

5

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 80170N-Hydroxysuccinimide

생성물 1

HCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

N-Boc-glycine (7.31 g, 41.7 mmol) was dissolved in 100 mL of DCM and to the cooled (15° C.) solution N-hydroxysuccinimide (5.28 g, 45.9 mmol) was added. N,N′-dicyclohexylcarbodiimide (9.47 g, 45.9 mmol) was added to the formed suspension under vigorous stirring. After a few seconds, a cloudy white suspension formed, the mixture was allowed to reach room temperature and stirred for 1 h. It was subsequently filtrated over celite, washed with 50 mL saturated sodium bicarbonate, dried over sodium sulfate and concentrated in vacuo to yield a crystalline powder. Yield: 7.02 g, 61.8%

후처리

  1. additionwas added
  2. waitAfter a few seconds
  3. customa cloudy white suspension formed
  4. customto reach room temperature
  5. filtrationIt was subsequently filtrated over celite
  6. washwashed with 50 mL saturated sodium bicarbonate
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customto yield a crystalline powder

출처 및 근거

ORD 기록
ord-5de66e3e0b704fb984cf6ce0ec846149
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346814B2

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