Phenyl chloroformate → Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate

HRID 1842972노트

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HRID 1842972 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:13])([CH2:11][OH:12])[CH2:9][OH:10])=[CH:4][CH:3]=1.Cl[C:15]([O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:16]>C([O-])(O)=O.[Na+].O.C1COCC1>[OH:10][CH2:9][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:15](=[O:16])[O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:7][CH:6]=1)([CH3:13])[CH2:11][OH:12]

참가 물질

6

반응물 2

HCID 15891Phenyl chloroformateHCID 594100922-(4-Aminophenyl)-2-methylpropane-1,3-diol

생성물 1

HCID 86672164Phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate수율 66.1%

시약·촉매·용매 3

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

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온도
0 °C

실험 절차

To a stirred solution of 2-(4-aminophenyl)-2-methylpropane-1,3-diol (1 g, 5.52 mmol, 1.0 eq) in sat. aq. NaHCO3 (4 mL), water (2 mL) and THF (4 mL) was added phenyl chloroformate (0.76 mL, 6.08 mmol, 1.1 eq) at 0° C. and the mixture was stirred at 0° C. for 0.5 h. The mixture was diluted with water (10 mL) and extracted with EtOAc (2×30 mL). The combined organic layer was washed with brine (10 mL) and the solvent evaporated. The crude product was purified by CC using chloroform/MeOH (95:5) as eluent to get phenyl 4-(1,3-dihydroxy-2-methylpropan-2-yl)phenylcarbamate (1.1 g, 60%) as a white solid (TLC system: chloroform—MeOH; 9:1; Rf: 0.4).

후처리

  1. extractionextracted with EtOAc (2×30 mL)
  2. washThe combined organic layer was washed with brine (10 mL)
  3. customthe solvent evaporated
  4. customThe crude product was purified by CC

출처 및 근거

ORD 기록
ord-a065c8adcd224eadbafb55228de82054
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

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