Sodium Hydroxide → HCID 11625348, compound

HRID 1365090Notes

Reaction equation

HRID 1365090 reaction equation
[OH-].[Na+].O=C1[N:9]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]([NH:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C:25](=[O:29])[CH2:24][CH2:23]4)=[O:18])[CH2:12][CH2:11]2)[C:8]2[CH:30]=[CH:31][CH:32]=[CH:33][C:7]=2[CH2:6][O:5]1>C(O)C>[OH:5][CH2:6][C:7]1[CH:33]=[CH:32][CH:31]=[CH:30][C:8]=1[NH:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]([NH:19][C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[C:25](=[O:29])[CH2:24][CH2:23]3)=[O:18])[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10253518HCID 10253518, compound

Product 1

HCID 11625348HCID 11625348, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

5 mL 10% sodium hydroxide were added to a suspension of 2-[4-(2-oxo-4H-benzo[d][1,3]oxazin-1-yl)-piperidine-1-yl]-N-(1-oxo-indan-5-yl)-acetamide (25 mg, 0.06 mmols) in 5 mL ethanol. The resulting mixture was heated to 50° C. for 2 hours, cooled, the ethanol was evaporated and the aqueous phase was neutralized and extracted with methylene chloride (2×15 mL). The combined organic extracts were washed with water, dried over sodium sulfate and evaporated to dryness. The crude material was purified via a silica gel column, eluting with ethyl acetate. 15 mg of a white solid were obtained, i.e. a yield of 64%.

Workup

  1. temperaturecooled
  2. customthe ethanol was evaporated
  3. extractionextracted with methylene chloride (2×15 mL)
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness
  7. customThe crude material was purified via a silica gel column
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-a8a649d7353a4a848b8caba75fa071d3
Source dataset
uspto-grants-2011_02
Patent number
US07888510B2

Reaction notes

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