Water → HCID 67107241, compound

HRID 1623676Notes

Reaction equation

HRID 1623676 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=1[O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]([OH:16])=O)=[O:10].[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1.O>ClCCl.CN(C)C=O>[C:22]1([CH2:21][O:20][C:19]2[CH:18]=[CH:17][C:13]([C:14]([N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[O:16])=[CH:12][C:11]=2[C:9]([O:8][CH3:7])=[O:10])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 31268PyrrolidineHCID 65578Oxalyl chlorideHCID 671067771285516-45-1

Product 1

HCID 67107241HCID 67107241, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (0.61 ml, 6.99 mmol) was added dropwise to a stirred solution of 3-[(methyloxy)carbonyl]-4-[(phenylmethyl)oxy]benzoic acid (may be prepared as described in Description 49; 400 mg, 1.40 mmol) in dichloromethane (10 ml) and dimethylformamide (3 drops) at room temperature. The mixture was stirred at room temperature for 1 h. The solvent was removed, and the residue was dissolved in dichloromethane (5 ml). This mixture was added to a solution of pyrrolidine (497 mg, 6.99 mmol) in dichloromethane (5 ml) and the mixture was stirred at room temperature for 2 h. Water (60 ml) was added, and the mixture was extracted with dichloromethane (3×60 ml). The organic phase was washed with saturated brine (50 ml), dried over sodium sulfate, and evaporated in vacuo to give the crude product. The crude product was loaded onto a silica gel column (200 g), and was eluted with dichloromethane/methanol=50:1 to yield the title compound as a colourless oil. 400 mg.

Workup

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in dichloromethane (5 ml)
  3. stirringthe mixture was stirred at room temperature for 2 h
  4. extractionthe mixture was extracted with dichloromethane (3×60 ml)
  5. washThe organic phase was washed with saturated brine (50 ml)
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto give the crude product
  9. washwas eluted with dichloromethane/methanol=50:1

Sources & evidence

ORD record
ord-11b8e55dad10449bb3b9442358bc5bd0
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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