Sodium hydride → (5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one

HRID 2118321노트

반응식

HRID 2118321 반응식
[H-].[Na+].[CH3:3][C:4]1([CH3:20])[O:9][C:8]2[CH:10]=[CH:11][C:12]([C@H:14]3[O:18][C:17](=[O:19])[NH:16][CH2:15]3)=[CH:13][C:7]=2[CH2:6][O:5]1.[I:21][C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][CH2:31][O:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]Br)[CH:25]=[CH:26][CH:27]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:3][C:4]1([CH3:20])[O:9][C:8]2[CH:10]=[CH:11][C:12]([C@H:14]3[O:18][C:17](=[O:19])[N:16]([CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][O:32][CH2:31][CH2:30][CH2:29][CH2:28][C:24]4[CH:25]=[CH:26][CH:27]=[C:22]([I:21])[CH:23]=4)[CH2:15]3)=[CH:13][C:7]=2[CH2:6][O:5]1

참가 물질

6

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 10933894(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-1,3-oxazolidin-2-oneHCID 691198836-Bromohexyl 4-(3-iodophenyl)butyl ether

생성물 1

HCID 69120002(5R)-5-(2,2-Dimethyl-4H-1,3-benzodioxin-6-yl)-3-{6-[4-(3-iodophenyl)butoxy]hexyl}-1,3-oxazolidin-2-one수율 73.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
50 °C

실험 절차

Sodium hydride (60% dispersion in oil 1.26 g) was added to a stirred, cooled (ice-bath) solution of (5R)-5-(2,2-dimethyl-4H-1,3-benzodioxin-6-yl)-2-oxazolidinone (5.47 g) in dry DMF (50 ml) under nitrogen and the mixture was stirred for 15 min at 50° C. A solution of 6-bromohexyl 4-(3-iodophenyl)butyl ether (10.7 g) in DMF (30 ml) was then added dropwise over 10 min. The mixture was stirred for 2 h at ambient temperature, then poured into aqueous solution of ammonium chloride and extracted into ethyl acetate. The combined extracts were washed with water, dried (Na2SO4) and evaporated. The residue was purified on biotage (90 g cartridge) eluting with ether-hexane (3:2) to give the title compound (9.8 g). LCMS RT=4.20 min.

후처리

  1. stirringThe mixture was stirred for 2 h at ambient temperature
  2. extractionextracted into ethyl acetate
  3. washThe combined extracts were washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified on biotage (90 g cartridge)
  7. washeluting with ether-hexane (3:2)

출처 및 근거

ORD 기록
ord-de1f4bb28dc541d7baf2ede4bb30bacc
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442839B2

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