Lithium Chloride → Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate

HRID 1842961노트

반응식

HRID 1842961 반응식
[F:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[CH:18]([C:23](OC)=[O:24])[C:19](OC)=[O:20].[BH4-].[Na+].[Cl-].[Li+]>C(O)C.C1COCC1>[OH:24][CH2:23][CH:18]([C:3]1[CH:4]=[CH:5][C:6]([NH:8][C:9](=[O:10])[O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:2]=1[F:1])[CH2:19][OH:20]

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 86672161Dimethyl 2-(2-fluoro-4-(phenoxycarbonylamino)phenyl)malonate

생성물 1

HCID 86672159Phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate수율 19%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a stirred solution of dimethyl 2-(2-fluoro-4-(phenoxycarbonylamino)phenyl)malonate (3.0 g, 8.31 mmol, 1.0 eq) in ethanol (15 mL) and THF (15 mL) was added NaBH4 (621 mg, 16.62 mmol, 2.0 eq) followed by lithium chloride (705 g, 16.62 mmol, 2.0 eq) at 0° C. and the mixture was stirred at 0° C. for 5 h. The solvent was evaporated and the residue diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic layer was separated, washed with brine, dried over Na2SO4 and evaporated. The residue was purified by CC using MeOH/DCM (1:19) as eluent to get phenyl 4-(1,3-dihydroxypropan-2-yl)-3-fluorophenylcarbamate (482 mg, 19%, white solid; TLC system: MeOH/DCM (1:9), Rf: 0.6)

후처리

  1. customThe solvent was evaporated
  2. additionthe residue diluted with water (30 mL)
  3. extractionextracted with EtOAc (2×50 mL)
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customThe residue was purified by CC

출처 및 근거

ORD 기록
ord-2c55536ac0464644b2641751dfe9d37f
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08946204B2

반응 노트

불러오는 중…