Ethyl Acetate → HCID 58923357, compound

HRID 1951047Notes

Reaction equation

HRID 1951047 reaction equation
[H-].[Na+].F[C:4]1[C:9]([F:10])=[CH:8][CH:7]=[CH:6][C:5]=1[C:11]([C:13]1[C:18]([OH:19])=[CH:17][C:16]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)=[CH:15][C:14]=1[OH:26])=[O:12].CCOC(C)=O>CN(C=O)C>[F:10][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:4]=1[O:26][C:14]1[CH:15]=[C:16]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[CH:17]=[C:18]([OH:19])[C:13]=1[C:11]2=[O:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 58923398HCID 58923398, compound

Product 1

HCID 58923357HCID 58923357, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Sodium hydride (24 mg, 1.0 mmol, 60%) was added to a solution of a compound of Example 24 (168 Mg, 0.50 mmol) in DMF (2 mL), then the mixture was heated at 75° C. for 4 h. The reaction was cooled to 22° C., and EtOAc (70 mL) was added to produce a yellow precipitate. The precipitate was filtered and dried to yield 10 mg (7%) of 5-fluoro-1-hydroxy-3-morpholin-4-yl-xanthen-9-one. 1H NMR (CDCl3, 400 MHz) δ: 12.59 (s, 1H), 7.95 (d, 1H), 7.75 (m, 1H), 7.40 (m, 1H), 6.60 (s, 1H), 6.38 (s, 1H), 3.65-3.63 (m, 4H), 3.40-3.38 (m, 4H). LRMS (APCI, positive): 316.3 (m+1).

Workup

  1. temperatureThe reaction was cooled to 22° C.
  2. customto produce a yellow precipitate
  3. filtrationThe precipitate was filtered
  4. customdried

Sources & evidence

ORD record
ord-380b5934bcc54df79bea223002b1a9d7
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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