Acetic Acid → HCID 178495912, compound

HRID 529189Notes

Reaction equation

HRID 529189 reaction equation
[F:1][C:2]1[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:3]=1[CH2:4][N:5]1[C:10]2[S:11][C:12]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][O:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)=[C:13]([CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:9]=2[C:8](=[O:33])[N:7]([C:34]2[N:35]=[N:36][C:37]([O:40]C)=[CH:38][CH:39]=2)[C:6]1=[O:42].Cl.C(O)(=O)C.C(=O)(O)[O-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:47][C:43]1[CH:44]=[CH:45][CH:46]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]1[C:10]2[S:11][C:12]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][O:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)=[C:13]([CH2:14][N:15]([CH2:16][CH2:17][O:18][CH3:19])[CH3:20])[C:9]=2[C:8](=[O:33])[N:7]([C:34]2[N:35]=[N:36][C:37]([OH:40])=[CH:38][CH:39]=2)[C:6]1=[O:42]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 59000866HCID 59000866, compound

Product 1

HCID 178495912HCID 178495912, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound (1.34 g, 2 mmol) obtained in Example 57 in THF (30 ml) was added a solution of 4N HCl in acetic acid (2 ml, 8 mmol), and the mixture was stirred at room temperature for 20 hours, at 50° C. for 10 hours and further at 60° C. for 3 hours. The reaction liquid was distributed between aqueous solution of sodium bicarbonate and ethyl acetate, and the organic layer was extracted. The aqueous layer was subjected to salting-out, and extracted with ethyl acetate. The organic layers were collected and combined and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by NH-silica gel (Produced by Fuji Silysia Chemical Ltd.) column chromatography (eluent;ethyl acetate/methanol=8/1). To the eluate was added diisopropylether to give powders. The powders were collected by filtration, washed with diisopropylether to obtain the title compound (539 mg, 41%) as a pale yellow powder.

Workup

  1. customThe reaction liquid
  2. extractionthe organic layer was extracted
  3. extractionextracted with ethyl acetate
  4. customThe organic layers were collected
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by NH-silica gel (Produced by Fuji Silysia Chemical Ltd.) column chromatography (eluent;ethyl acetate/methanol=8/1)
  8. additionTo the eluate was added diisopropylether
  9. customto give powders
  10. filtrationThe powders were collected by filtration
  11. washwashed with diisopropylether

Sources & evidence

ORD record
ord-44eac106ca5a4a338500e0202fd2fb81
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

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