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tert-Butanol → HCID 86753233, compound

HRID 399858
Notes
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Reaction equation

HRID 399858 reaction equation
C(CC[C:6]1[CH:7]=[C:8]([CH:13]=[C:14]([N:16]2[CH:20]=[CH:19][CH:18]=[CH:17]2)[CH:15]=1)[C:9]([O:11][CH3:12])=[O:10])(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:28])C=CC=CC=1.C([N:40]([CH2:43]C)[CH2:41]C)C.C(OCC)(=O)C.[C:51]([OH:55])([CH3:54])([CH3:53])[CH3:52]>O>[C:51]([O:55][C:43]([NH:40][CH2:41][CH2:12][O:11][C:9](=[O:10])[C:8]1[CH:13]=[C:14]([N:16]2[CH:17]=[CH:18][CH:19]=[CH:20]2)[CH:15]=[CH:6][CH:7]=1)=[O:28])([CH3:54])([CH3:53])[CH3:52]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 18945165HCID 18945165, compound

Product 1

HCID 86753233HCID 86753233, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-(2-carboxyethyl)-5-(pyrrol-1-yl)benzoate (1.5 g), diphenylphosphoryl azide (1.25 ml) and triethylamine (0.8 ml) in tert-butyl alcohol (20 ml) was refluxed for 7 hours. After being cooled to room temperature, the reaction mixture was poured into a mixture of ethyl acetate and water. The organic layer was successively washed with 1N-hydrochloric acid, water and brine and dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was purified by column chromatography on silica gel eluting with chloroform. The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-(2-tert-butoxycarbonylaminoethyl-5-(pyrrol-1-yl)benzoate (0.89 g).

Workup

  1. temperaturewas refluxed for 7 hours
  2. washThe organic layer was successively washed with 1N-hydrochloric acid, water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customthe residue was purified by column chromatography on silica gel eluting with chloroform
  6. additionThe eluted fractions containing the desired product
  7. customwere collected
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-4b5878e6a797463f839eabba0397be70
Source dataset
uspto-grants-1998_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05824691

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes