Water → HCID 21631641, compound

HRID 383914Notes

Reaction equation

HRID 383914 reaction equation
[C:1]1([C:7]2[S:8][CH:9]=[CH:10][C:11]=2C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C=CC(P([N:29]=[N+]=[N-])(C2C=CC=CC=2)=O)=CC=1.C[C:33]([OH:36])(C)C.[OH2:37].[C:38]1([CH3:44])[CH:43]=CC=C[CH:39]=1>>[C:1]1([C:7]2[S:8][CH:9]=[CH:10][C:11]=2[NH:29][C:33](=[O:36])[O:37][C:38]([CH3:44])([CH3:43])[CH3:39])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 5

HCID 962WaterHCID 1140Toluene2×HCID 6386tert-ButanolHCID 199401P,P-Diphenylphosphinic azideHCID 8485112-phenyl-3-thiophenecarboxylic acid

Product 1

HCID 21631641HCID 21631641, compound

Procedure

To a solution of 2-phenylthiophene-3-carboxylic acid and TEA in toluene was added dropwise a solution of DPPA in toluene, followed by stirring at room temperature for 40 minutes, and then stirring at 90° C. for 60 minutes. To this solution was added tBuOH, followed by heating under reflux for 15 hours. To the reaction solution was added water, followed by extraction with EtOAc. The organic layer was washed with water and brine in this order, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain tert-butyl (2-phenyl-3-thienyl)carbamate as a pale brown oil.

Workup

  1. stirringstirring at 90° C. for 60 minutes
  2. temperatureby heating
  3. temperatureunder reflux for 15 hours
  4. extractionfollowed by extraction with EtOAc
  5. washThe organic layer was washed with water and brine in this order
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by medium-pressure preparative liquid chromatography (silica gel, YAMAZEN YFLC WPrep2XY, hexane:EtOAc)

Sources & evidence

ORD record
ord-e71d5c8e44e241ce962a4d422586b6cf
Source dataset
uspto-grants-2013_02
Patent number
US08367696B2

Reaction notes

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