Dimethylformamide → HCID 57672611, compound

HRID 1192854Notes

Reaction equation

HRID 1192854 reaction equation
S(Cl)(Cl)=O.[C:5]([O:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=O)=[CH:15][CH:14]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C[N:26](C=O)C>>[C:5]([O:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][CH2:21][C:22]([NH2:26])=[O:24])=[CH:15][CH:14]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 2755933HCID 2755933, compound

Product 1

HCID 57672611HCID 57672611, compoundYield 82%

Conditions

Temperature
-5 °C

Procedure

Thionyl chloride (0.22 mL, 3.01 mmol) was added slowly to a solution of 4-[4-(t-Butoxycarbonylamino)phenyl]butanoic acid (100) (0.70 g, 2.51 mmol) in DMF (5 mL) cooled at −5° C. The mixture was stirred for an additional 1 h at −5° C. Excess ammonia (freshly distilled from its aqueous solution) was added to the reaction medium. The second mixture was stirred for an additional 1 h. Ethyl acetate (50 mL) was added to the mixture, which was washed with brine (2×50 mL). The organic layer was dried over MgSO4, concentrated and the residue was purified by silica gel column chromatography (dichloromethane:acetone, 9:1) to give 4-[4-(t-Butoxycarbonylamino)phenyl]butanamide (99) (0.57 g, 82%) as a white solid.

Workup

  1. distillationExcess ammonia (freshly distilled from its aqueous solution)
  2. additionwas added to the reaction medium
  3. stirringThe second mixture was stirred for an additional 1 h
  4. additionEthyl acetate (50 mL) was added to the mixture, which
  5. washwas washed with brine (2×50 mL)
  6. dry with materialThe organic layer was dried over MgSO4
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel column chromatography (dichloromethane:acetone, 9:1)

Sources & evidence

ORD record
ord-d7a10ae0b74448e49ea88e8e0070bd08
Source dataset
uspto-grants-2014_03
Patent number
US08680291B2

Reaction notes

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