Water → HCID 86600460, compound

HRID 1669922Notes

Reaction equation

HRID 1669922 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]([NH:11][C:12](OC(C)(C)C)=O)([CH3:10])[CH2:8][F:9])([CH3:4])([CH3:3])[CH3:2].CI.[H-].[Na+].[OH2:24]>CN(C=O)C>[C:1]([O:5][C:6](=[O:19])[C:7]([NH:11][CH2:12][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:24])([CH3:10])[CH2:8][F:9])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 10880397HCID 10880397, compound

Product 1

HCID 86600460HCID 86600460, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3 (200 mg, 0.72 mmol) in dry DMF under an argon atmosphere was added 8 eq of CH3I (0.36 mL) followed by 2 eq of 95% NaH (37 mg). The reaction mixture was stirred overnight at room temperature. The reaction mix was added to 15 mL of H2O and extracted with 3×15 mL of Et2O. The combined organic layers were washed with 3×20 mL H2O followed by the usual work up. Purification of the crude product via silica gel column chromatography (7.5% EtOAc in hexane) afforded the methylated species 4 (181 mg, 86%) as a colorless oil: 1H NMR (CDCl3) δ 1.44 (9H, s), 1.46 (9H, s), 1.51 (3H, s), 2.94 (3H, s), 4.51-5.04 (2H, m). Anal. (C14H26FNO4) C, H, N.

Workup

  1. additionThe reaction mix
  2. extractionextracted with 3×15 mL of Et2O
  3. washThe combined organic layers were washed with 3×20 mL H2O
  4. customPurification of the crude product via silica gel column chromatography (7.5% EtOAc in hexane)

Sources & evidence

ORD record
ord-99cbc8b6331f45d59f31d51801300956
Source dataset
uspto-grants-2011_08
Patent number
US07989649B2

Reaction notes

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