Sodium Hydroxide → HCID 69066344, compound

HRID 229379Notes

Reaction equation

HRID 229379 reaction equation
C(=O)(OCC)[O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=3)[N:15]3[C:23]([C:26]#[N:27])=[CH:24][CH:25]=[C:14]3[CH:13]2[CH2:28][CH3:29])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[OH-:34].[Na+]>C(O)C>[CH2:28]([CH:13]1[N:12]([S:9]([C:6]2[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=2)(=[O:11])=[O:10])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([F:22])[CH:20]=2)[N:15]2[C:23]([C:26]([NH2:27])=[O:34])=[CH:24][CH:25]=[C:14]12)[CH3:29]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69068852HCID 69068852, compound

Product 1

HCID 69066344HCID 69066344, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.25 g (0.53 mmol) of the product from Example 34 was dissolved in 15 ml of ethanol and 5 ml of 2N NaOH was added. The solution was heated to reflux for 3 hours, after which time it was concentrated then neutralized with 2N HCl. The mixture was extracted with ethyl acetate (2×20 ml) and the combined organic layers were dried (MgSO4) and concentrated. The crude solid was subjected to column chromatography on silica gel eluting with chloroform:methanol (95:5). The fractions containing product were combined and concentrated to yield a light tan solid, which was crystallized from ethyl acetate:hexane to yield 32 mg (14%) of product, mp 168-170° C. (d).

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 hours
  3. concentrationafter which time it was concentrated
  4. extractionThe mixture was extracted with ethyl acetate (2×20 ml)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated
  7. additionThe fractions containing product
  8. concentrationconcentrated
  9. customto yield a light tan solid, which
  10. customwas crystallized from ethyl acetate

Sources & evidence

ORD record
ord-9613abbc23dc456d93152600130ac7bc
Source dataset
uspto-grants-2009_07
Patent number
US07563793B2

Reaction notes

Loading…