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

HRID 369364
Notes
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Reaction equation

HRID 369364 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ec41396f73a74cf6b46d3bd50a478c3b
Source dataset
uspto-grants-2000_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06136852

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes