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Chloroacetyl chloride → HCID 66973294, 화합물

HRID 1864897
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HRID 1864897 반응식
[NH2:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:11].C(N(CC)CC)C.[Cl:19][CH2:20][C:21](Cl)=[O:22]>C(Cl)Cl>[Cl:19][CH2:20][C:21]([NH:1][C@@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@@H:3]1[OH:11])=[O:22]
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참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2725045(1R,2S)-(+)-cis-1-Amino-2-indanol

생성물 1

HCID 66973294HCID 66973294, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a mixture of (1R,2S)-1-amino-2-indanol (500 mg, 3.35 mmol) and triethylamine (0.51 mL, 3.69 mmol) in anhydrous CH2Cl2 at 0° C. was added chloroacetyl chloride (0.295 mL, 3.69 mmol) dropwise. The resulting mixture was stirred for 30 min, quenched with saturated aqueous NaHCO3 (15 mL) and then extracted with EtOAc (2×75 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc 70:30 to 0:100, to give the title compound. MS: m/z=226 (M+1).

후처리

  1. customquenched with saturated aqueous NaHCO3 (15 mL)
  2. extractionextracted with EtOAc (2×75 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of hexane:EtOAc 70:30 to 0:100

출처 및 근거

ORD 기록
ord-85f2a33303a54722b9217dd9a9fa168b
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07625901B2

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