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Ethylene Glycol → HCID 53820814, 화합물

HRID 1386799
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HRID 1386799 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:27])[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[CH2:28](O)[CH2:29][OH:30].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2([O:30][CH2:29][CH2:28][O:27]2)[CH2:9][CH2:10][CH:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[CH2:13][CH2:12]2)=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acid2회HCID 57210991HCID 57210991, 화합물

생성물 1

HCID 53820814HCID 53820814, 화합물수율 84%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 71 mg (0.19 mmol) of 4-(3-(4-fluorophenyl)-3-oxo-propyl)-1-(benzyloxycarbonyl) piperidine (from EXAMPLE 189, Step B), 0.05 mL (0.9 mmol) of ethylene glycol and 5 mg (0.26 mmol) of p-toluene sulfonic acid x H2O in 3 mL of toluene was heated at 80° C. After 1 h, and additional 5 mg of p-toluene sulfonic acid×H2O was added and the resulting mixture was heated at reflux. After 2 h, the mixture was cooled and partitioned between 30 mL of ether and 10 mL of 1.0 N NaOH. The organic layer was separated, dried and concentrated. Flash chromatography on 4 g of silica gel using 3:1 v/v hexanes/ether afforded 66 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.00-1.10 (m, 2H), 1.261.36 (3H), 1.50-1.60 (m, 2H), 1.86-1.89 (m, 2H), 2.65-2.75 (m, 2H), 3.71-3.78 (m, 2H), 3.96-4.03 (m, 2H), 4.064.16 (m, 2H), 5.10 (s, 2H), 6.99-7.04 (m, 2H), 7.26-7.40 (7H).

후처리

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux
  3. waitAfter 2 h
  4. temperaturethe mixture was cooled
  5. custompartitioned between 30 mL of ether and 10 mL of 1.0 N NaOH
  6. customThe organic layer was separated
  7. customdried
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bac6ebc39a894909ae377d24e125becc
출처 데이터셋
uspto-grants-2001_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06265434B1

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