Potassium Phosphate, Tribasic → ethyl (S)-5-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]valerate

HRID 369364

반응식

HRID 369364 반응식
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][CH2:3][CH:4]=[CH2:5].C12BC(CCC1)CCC2.FC(F)(F)S(O[C:25]1[CH:34]=[C:33]2[C:28]([CH2:29][CH2:30][C@H:31]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32]2)=[CH:27][CH:26]=1)(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.O1CCOCC1>[C:39]([O:38][C:36]([NH:35][C@H:31]1[CH2:30][CH2:29][C:28]2[C:33](=[CH:34][C:25]([CH2:5][CH2:4][CH2:3][CH2:2][C:1]([O:7][CH2:8][CH3:9])=[O:6])=[CH:26][CH:27]=2)[CH2:32]1)=[O:37])([CH3:42])([CH3:40])[CH3:41]

참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 74786Ethyl 4-pentenoateHCID 789669-Borabicyclo(3.3.1)nonaneHCID 18651771(S)-2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl trifluoromethanesulfonate

생성물 1

HCID 86755955ethyl (S)-5-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]valerate수율 45.8%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 312751,4-Dioxane용매

실험 절차

Ethyl 4-pentenoate (317 mg) was dissolved in tetrahydrofuran (5 ml), and 9-borabicyclo[3.3.1]nonane (302 mg) was added to the solution. After reaction for 15 hours at room temperature with stirring, 1,4-dioxane (9 ml), (S)-2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl trifluoromethanesulfonate (890 mg), tetrakis(triphenylphosphine)palladium (0) (65 mg) and potassium phosphate (716 mg) were added to the reaction mixture, followed by reaction for 15 hours at 85° C. with stirring. Water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, then the solvent was removed in vacuo. Purification by medium pressure liquid column chromatography on silica gel (eluent: dichloromethane) and sequential recrystallization from hexane of the residue gave ethyl (S)-5-[2-(tert-butoxycarbonylamino)-1,2,3,4-tetrahydronaphthalen-7-yl]valerate (387 mg) having a melting point of 65-67° C.

후처리

  1. customAfter reaction for 15 hours at room temperature
  2. customfollowed by reaction for 15 hours at 85° C.
  3. stirringwith stirring
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customPurification by medium pressure liquid column chromatography
  9. customon silica gel (eluent: dichloromethane) and sequential recrystallization from hexane of the residue

출처 및 근거

ORD 기록
ord-ec41396f73a74cf6b46d3bd50a478c3b
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136852

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