Sodium hydride → HCID 56643814, compound

HRID 2040873Notes

Reaction equation

HRID 2040873 reaction equation
[C:1]1([C:7]#[C:8][C:9]2[CH2:13][C:12]3([CH2:18][CH2:17][C:16](=[N:19][OH:20])[CH2:15][CH2:14]3)[O:11][N:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH:24]1[CH2:29][CH2:28][O:27][C:25]1=[O:26]>C1COCC1>[O:26]=[C:25]1[CH:24]([O:20][N:19]=[C:16]2[CH2:17][CH2:18][C:12]3([O:11][N:10]=[C:9]([C:8]#[C:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:13]3)[CH2:14][CH2:15]2)[CH2:29][CH2:28][O:27]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 954632(3H)-Furanone, 3-bromodihydro-HCID 56646685HCID 56646685, compound

Product 1

HCID 56643814HCID 56643814, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound of Example 46 (50 mg, 0.186 mmol) in THF (5 mL) was added sodium hydride (60% oil dispersion, 7.81 mg, 0.195 mmol) and the mixture was stirred at r.t. for 1 h. Afterwards, 2-bromo-gamma-butyrolactone (17.2 μL, 0.186 mmol) was added and the reaction was stirred overnight, quenched with water, extracted with EtOAc. The combined organic layers were washed with brine, evaporated to dryness in vacuo to afford a crude, which was purified by automated RP chromatography (Isolera®TM-Biotage; gradient buffer NH4HCO3-MeCN from 40-60 a 30-70. Yield: 32%

Workup

  1. stirringthe reaction was stirred overnight
  2. customquenched with water
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customevaporated to dryness in vacuo
  6. customto afford a crude, which
  7. customwas purified by automated RP chromatography (Isolera®TM-Biotage

Sources & evidence

ORD record
ord-75c58168f9ef40c0bbbe63f6d87c25bd
Source dataset
uspto-grants-2013_11
Patent number
US08580962B2

Reaction notes

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