Acetic Acid → HCID 58295100, compound

HRID 2045823Notes

Reaction equation

HRID 2045823 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C@H:18]3[C@H:22]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=4[F:31])[CH2:21][N:20]([C:32]4[N:33]=[N:34][C:35](Cl)=[CH:36][CH:37]=4)[CH2:19]3)=[O:17])[CH2:11][CH2:10][N:9]2[S:39]([CH3:42])(=[O:41])=[O:40])=[CH:4][CH:3]=1.C(O)(=[O:45])C>>[NH3:9].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([C@H:18]3[C@H:22]([C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][C:24]=4[F:31])[CH2:21][N:20]([C:32]4[CH:37]=[CH:36][C:35](=[O:45])[NH:34][N:33]=4)[CH2:19]3)=[O:17])[CH2:11][CH2:10][N:9]2[S:39]([CH3:42])(=[O:40])=[O:41])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 58295104HCID 58295104, compound

Product 2

HCID 222AmmoniaHCID 58295100HCID 58295100, compoundYield 93%

Procedure

The compound of example 108 (100 mg, 0.157 mmol) was dissolved in acetic acid (5 mL). The resulting solution was thoroughly degassed and stirred at reflux under nitrogen overnight. The reaction was concentrated in vacuo and residue diluted by adding sodium hydrogen carbonate solution (25 mL) and extracted with EtOAc (3×25 mL). The combined organic extracts were washed with sodium hydrogen carbonate solution (30 mL), brine (30 mL), dried with sodium sulphate, filtered and concentrated in vacuo to give the crude residue. Purification by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (92.5:7.5:0.75) gave 90 mg (93%) of the title compound as a mixture of epimers as an off white foam.

Workup

  1. customThe resulting solution was thoroughly degassed
  2. temperatureat reflux under nitrogen overnight
  3. concentrationThe reaction was concentrated in vacuo and residue
  4. additiondiluted
  5. additionby adding sodium hydrogen carbonate solution (25 mL)
  6. extractionextracted with EtOAc (3×25 mL)
  7. washThe combined organic extracts were washed with sodium hydrogen carbonate solution (30 mL), brine (30 mL)
  8. dry with materialdried with sodium sulphate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give the crude residue
  12. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-561453e6691d4a0abcaeefa692224f2c
Source dataset
uspto-grants-2013_11
Patent number
US08592403B2

Reaction notes

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