Diisopropylcarbodiimide → Tert-butyl n-(2-tert-butoxy-2-oxoethyl)-n-[(1-oxo-2,3-dihydro-1h-inden-4-yl)carbonyl]glycinate

HRID 2377235노트

반응식

HRID 2377235 반응식
[O:1]=[C:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([C:11]([OH:13])=O)[C:5]=2[CH2:4][CH2:3]1.C(N=C=NC(C)C)(C)C.O.ON1C2C=CC=CC=2N=N1.[NH:34]([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37]>ClCCl>[C:39]([O:38][C:36](=[O:37])[CH2:35][N:34]([C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2=[O:1])=[O:13])[CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])([CH3:42])([CH3:41])[CH3:40]

참가 물질

6

반응물 4

HCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 4393691DI-T-Butyl iminodiacetateHCID 125422061-Oxo-indan-4-carboxylic acid

생성물 1

HCID 69199393Tert-butyl n-(2-tert-butoxy-2-oxoethyl)-n-[(1-oxo-2,3-dihydro-1h-inden-4-yl)carbonyl]glycinate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of Example 5 (500 mg, 2.84 mmol) in dichloromethane (10 mL) was added 1,3-diisopropylcarbodiimide (0.44 mL, 2.84 mmol), 1-hydroxybenzotriazole hydrate (115 mg, 0.85 mmol), and di-t-butyl iminodiacetate (1.04 g, 4.26 mmol). The mixture was stirred at room temperature for about 24 hours, quenched with water, and extracted with diethyl ether. The combined organic extracts were washed with brine and saturated aqueous sodium bicarbonate, dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by flash column chromatography on silica gel using hexane/ethyl acetate (1:1) as the mobile phase to provide the desired product. MS (ESI): m/z 402 (M−H)−.

후처리

  1. customquenched with water
  2. extractionextracted with diethyl ether
  3. washThe combined organic extracts were washed with brine and saturated aqueous sodium bicarbonate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by flash column chromatography on silica gel

출처 및 근거

ORD 기록
ord-e9763ea8365e433ba9448b2738d6e063
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07468371B2

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