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Potassium Hydroxide → 2-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester

HRID 352442
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HRID 352442 반응식
[OH-].[K+].[C:3]([O:7][C:8](=[O:31])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:12][CH:11]=1)([CH3:6])([CH3:5])[CH3:4].[CH2:32]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42]Br)[CH3:33]>CS(C)=O>[CH2:32]([O:34][C:35](=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42][N:9]([C:8]([O:7][C:3]([CH3:6])([CH3:4])[CH3:5])=[O:31])[C:10]1[CH:11]=[CH:12][C:13]([O:16][CH2:17][CH2:18][C:19]2[N:20]=[C:21]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[O:22][C:23]=2[CH3:24])=[CH:14][CH:15]=1)[CH3:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 11032082Ethyl 2-(bromomethyl)benzoateHCID 69486797{4-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester

생성물 1

HCID 694866072-[(Tert-butoxycarbonyl-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-amino)-methyl]-benzoic acid ethyl ester수율 94%

시약·촉매·용매 1

HCID 679
Dimethyl Sulfoxide
용매
2회

실험 절차

To a suspension of 3.41 g of powdered KOH in 110 ml of DMSO was added at 22° C. 6.00 g of {4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-carbamic acid tert-butyl ester and the suspension was stirred for 25 min. A solution of 7.40 g of 2-bromomethyl-benzoic acid ethyl ester in 10 ml of DMSO was added slowly keeping the temperature at 15-20° C. and stirring was continued at 22° C. for 2.5 h. The dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt, the organic layer was washed with saturated aqueous NH4Cl and water, dried and evaporated. The residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1) to give 7.96 g of the title compound as a pale yellow oil. MS: (M+H)+ 557.3.

후처리

  1. additionwas added at 22° C
  2. customat 15-20° C.
  3. customThe dark mixture was partitioned between 500 ml of a saturated aqueous NH4Cl and 200 ml of AcOEt
  4. washthe organic layer was washed with saturated aqueous NH4Cl and water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by chromatography (SiO2, n-hexane/AcOEt 4:1)

출처 및 근거

ORD 기록
ord-916188e7e8ba4087be5d272a3211af8f
출처 데이터셋
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06747049B2

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