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Hydroxylamine → 6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-hydroxyhexanamide

HRID 251700
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HRID 251700 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24](O)=[O:25])=[O:17].C(N(CC)CC)C.ClC(OCC)=O.[NH2:43][OH:44]>[Cl-].[Na+].O.CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[CH:14]=[C:15]([CH:27]=[CH:28][CH:29]=1)[C:16]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:43][OH:44])=[O:25])=[O:17]
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참가 물질

7

반응물 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 690325116-(3-((5-Fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid

생성물 1

HCID 766038976-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)-N-hydroxyhexanamide수율 41%

시약·촉매·용매 2

HCID 6228
Dimethylformamide
용매
HCID 57417360Sodium chloride; water용매

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온도
0 °C

실험 절차

6-(3-((5-fluoro-2-oxoindolin-3-ylidene)methyl)benzamido)hexanoic acid (396 mg, 1 mmol), triethylamine (151 mg, 1.5 mmol) and 20 ml of DMF were stirred at 0° C. while ethyl chloroformate (163 mg, 1.5 mmol) was added. The mixture was stirred at 0° C. for 2 hours, and then 50% aqueous solution of hydroxylamine (1.32 g, 20 mmol) was added. The mixture was stirred for 3 hours at room temperature, and then diluted with 1000 mL of brine. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (168 mg, 41%) as a brown solid. LC-MS (m/z) 412 (M+1).

후처리

  1. additionwas added
  2. stirringThe mixture was stirred for 3 hours at room temperature
  3. filtrationThe solids were collected by vacuum filtration
  4. washwashed with water
  5. customdried under vacuum

출처 및 근거

ORD 기록
ord-656c9f2bc79d4c118a23f618e9365f65
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07863315B2

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