Water → HCID 69095144, compound

HRID 2196561Notes

Reaction equation

HRID 2196561 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=2)[CH2:14][NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:9]=[C:8]([C:26]([F:29])([F:28])[F:27])[CH:7]=1.[H-].[Na+].O.[CH2:33]1COCC1>>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=2)[CH2:14][N:15]([CH3:33])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:19])[CH3:20])[N:9]=[C:8]([C:26]([F:29])([F:27])[F:28])[CH:7]=1

Participants

5

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 69095020HCID 69095020, compound

Product 1

HCID 69095144HCID 69095144, compoundYield 88%

Conditions

Temperature
21 °C

Procedure

To a stirred solution of 55 (3.51 g, 8.62 mmol) in THF (43 ml) was added NaH (0.689 g, 17.23 mmol). After 15 minutes Mel (2.69 ml, 43.1 mmol) was added and the resulting suspension was allowed to stir at 0° C. for 1 h and at 21° C. for 16 h. Water was added the product was extracted with EtOAc. After the usual work-up the residue was purified via Biotage (5% to 45% EtOAc/Hexane; 40+M column) to afford 138 (3.2 g, 7.59 mmol, 88% yield) as colorless oil. LRMS (ESI): (calc.) 421.4; (found) 444.2 (MNa)+.

Workup

  1. additionAfter 15 minutes Mel (2.69 ml, 43.1 mmol) was added
  2. extractionwas extracted with EtOAc
  3. customAfter the usual work-up the residue was purified via Biotage (5% to 45% EtOAc/Hexane; 40+M column)

Sources & evidence

ORD record
ord-1559a148a399400c9ac4e5546b0e299f
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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