Hydroxylamine → 6-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyhexanamide

HRID 1926191노트

반응식

HRID 1926191 반응식
[CH:1]1[C:13]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([OH:25])=O)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.ClC(OCC)=O.[NH2:39][OH:40]>[Cl-].[Na+].O.CN(C=O)C>[CH:10]1[C:11]2[C:12](=[CH:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([NH:39][OH:40])=[O:25])=[O:16])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

참가 물질

7

반응물 4

HCID 787HydroxylamineHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 574954166-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid

생성물 1

HCID 99245436-(2-(9H-fluoren-9-ylidene)acetamido)-N-hydroxyhexanamide수율 42%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
0 °C

실험 절차

6-(2-(9H-fluoren-9-ylidene)acetamido)hexanoic acid (335 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 (147 mg, 42%) as a yellow solid. 1H NMR (DMSO-d6) δ1.19 (m, 2H, CH2), 1.30 (m, 2H, CH2), 1.48 (m, 2H, CH2), 1.92 (t, J=8.0 Hz, 2H, CH2CO), 3.24 (m, 2H, NCH2), 7.08 (s, 1H, ═CH—CO), 7.28 (m, 2H, Ar—H), 7.41 (m, 2H, Ar—H), 7.76 (m, 1H, Ar—H), 7.81 (m, 2H, Ar—H), 8.53 (t, J=4.0 Hz, 1H, CONH), 8.67 (d, J=8.0 Hz, 1H, Ar—H), 10.32 (s, 1H, NH—O). LC-MS (m/z) 351 (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-4e98b7e59e1f4896962dca486b00dd7f
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178577B2

반응 노트

불러오는 중…