Ethylparaben → HCID 86587778, 화합물

HRID 354269노트

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HRID 354269 반응식
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].O[C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@H:9]1[CH2:10][O:11][C:16]1[CH:26]=[CH:25][C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:18][CH:17]=1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

참가 물질

6

반응물 4

HCID 8434EthylparabenHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643448(S)-(-)-N-Boc-prolinol

생성물 1

HCID 86587778HCID 86587778, 화합물수율 96.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

8,9 and 10 To a stirred mixture of Boc-prolinol (3.00 g, 14.9 mmol), ethyl p-hydroxybenzoate (2.40 g, 14.5 mmol), and triphenylphosphine (3.91 g, 14.9 mol) in THF (80 mL) was added dropwise diethyl azodicarboxylate (2.86 g, 16.4 mmol) at room temp. After the addition was completed, the resulting mixture was heated under reflux for 2 hr. After cooling, the mixture was concentrated in vacuo. The residue was dissolved in EtOAc and washed successively with 1 N NaOH, water, brine. The EtOAc layer was dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:4, v/v) as eluent to give 4.88 g (93%) ethyl (S)-4-(1-tert-butoxycarbonyl-2-pyrrolidinyl)methoxybenzoate as an oil.

후처리

  1. additionAfter the addition
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 2 hr
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated in vacuo
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed successively with 1 N NaOH, water, brine
  8. dry with materialThe EtOAc layer was dried over MgSO4
  9. customevaporated in vacuo
  10. customThe residue was purified by column chromatography on silica gel with EtOAc-n-hexane (1:4, v/v) as eluent

출처 및 근거

ORD 기록
ord-cf8190796b304f9ebe905a15cc455aeb
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06756378B2

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