Potassium Hydroxide → HCID 86669378, compound

HRID 537359Notes

Reaction equation

HRID 537359 reaction equation
[OH:1][C:2]1([C:41]2[CH:55]=[CH:54][CH:53]=[CH:52][C:42]=2[O:43][CH2:44][CH2:45][CH2:46][C:47]([O:49]CC)=[O:48])[CH2:7][CH2:6][N:5]([C:8]([C@:10]2([O:31][C:32]3[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[S:34][CH:33]=3)[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:27])[C:17]3[C:22]([C:23]([F:26])([F:25])[F:24])=[CH:21][CH:20]=[N:19][CH:18]=3)[C@@H:11]2[CH2:28][CH2:29][CH3:30])=[O:9])[CH2:4][CH2:3]1.[OH-].[K+]>CO.CCOC(C)=O>[OH:1][C:2]1([C:41]2[CH:55]=[CH:54][CH:53]=[CH:52][C:42]=2[O:43][CH2:44][CH2:45][CH2:46][C:47]([OH:49])=[O:48])[CH2:3][CH2:4][N:5]([C:8]([C@:10]2([O:31][C:32]3[CH:36]=[C:35]([C:37]([F:40])([F:38])[F:39])[S:34][CH:33]=3)[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:27])[C:17]3[C:22]([C:23]([F:24])([F:26])[F:25])=[CH:21][CH:20]=[N:19][CH:18]=3)[C@@H:11]2[CH2:28][CH2:29][CH3:30])=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 86669379HCID 86669379, compound

Product 1

HCID 86669378HCID 86669378, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To 86 (40 mg, 0.05 mmol, 1 eq) in MeOH was added KOH (3.5N, 5 equiv). Reaction was brought to 65° C. for 1 hour then cooled down to 23° C. Reaction was diluted with EtOAc, washed with sat. NH4Cl and brine. The organic layer was dried over MgSO4, filtered and concentrated down. HPLC purification, C18, CH3CN/H2O, 70% to 100% CH3CN provided 37 mg (100% yield) of product A91.

Workup

  1. customReaction
  2. customReaction
  3. washwashed with sat. NH4Cl and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated down
  7. customHPLC purification, C18, CH3CN/H2O, 70% to 100% CH3CN

Sources & evidence

ORD record
ord-00bb87d4a39a4a34a086c6b9366f751a
Source dataset
uspto-grants-2014_10
Patent number
US08859776B2

Reaction notes

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