Water → (+/-)-cis-({3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}oxy)acetic acid tert-butyl ester

HRID 2189037노트

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HRID 2189037 반응식
[C:1]1([C:7]2[O:23][C:10]3[N:11]=[CH:12][N:13]=[C:14]([NH:15][C@@H:16]4[CH2:21][CH2:20][CH2:19][C@H:18]([OH:22])[CH2:17]4)[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[C:26]([O:30][C:31](=[O:34])[CH2:32]Br)([CH3:29])([CH3:28])[CH3:27].O>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C1COCC1>[C:26]([O:30][C:31](=[O:34])[CH2:32][O:22][C@H:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([NH:15][C:14]2[C:9]3[CH:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:23][C:10]=3[N:11]=[CH:12][N:13]=2)[CH2:17]1)([CH3:29])([CH3:28])[CH3:27]

참가 물질

8

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 86653748(+/-)-cis-3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol

생성물 1

HCID 86653749(+/-)-cis-({3-[(6-Phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexyl}oxy)acetic acid tert-butyl ester

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

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온도
70 °C

실험 절차

At 40° C., add approx. 0.06 mmol of tetrabutylammonium hydrogensulphate and a solution of 200 mg (0.646 mmol) of (+/−)-cis-3-[(6-phenylfuro[2,3-d]pyrimidin-4-yl)amino]cyclohexanol in 0.5 ml of toluene and 0.1 ml of THF to a mixture of 517 mg of 50% sodium hydroxide solution (6.5 mmol) and 0.5 ml of toluene. Admix the resulting mixture with 0.19 ml (1.29 mmol) of bromoacetic acid tert-butyl ester with vigorous stirring and heat it to 70° C. After 2 h, cool the mixture and add it to water. Extract three times with dichloromethane, wash the combined organic phases with saturated sodium chloride solution and concentrate under reduced pressure. After preparative RP-HPLC (eluent: acetonitrile/water), 152 mg (55.5% of theory) of the target product are isolated from the crude product.

후처리

  1. temperaturecool the mixture
  2. extractionExtract three times with dichloromethane
  3. washwash the combined organic phases with saturated sodium chloride solution
  4. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-b14def8bf2cc47f3aa2c0a7633a384bc
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324222B2

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