Dimethylformamide → HCID 59385197, compound

HRID 2356824Notes

Reaction equation

HRID 2356824 reaction equation
[CH3:1][C:2]([C:22]([O:24][CH3:25])=[O:23])([CH3:21])[NH:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:8][CH:7]=1)=[O:5].[H-].[Na+].[CH3:28]N(C)C=O.IC>O>[CH3:28][N:3]([C:4]([C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)=[CH:10][CH:11]=1)=[O:5])[C:2]([CH3:1])([C:22]([O:24][CH3:25])=[O:23])[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59385205HCID 59385205, compound

Product 1

HCID 59385197HCID 59385197, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As shown in Reaction Scheme 11, a mixture of methyl 2-methyl-N-[(4′-nitrobiphenyl-4-yl)carbonyl]alaninate (1.32 g, 3.9 mmol), sodium hydride (117 mg, 4.6 mmol), and N,N-dimethylformamide (15 mL) was stirred for 2 h at rt. Iodomethane (0.48 mL, 7.7 mmol) was added, and the reaction mixture was stirred overnight at rt. Water (30 mL) was added, and the mixture was extracted with ethyl acetate (2×10 mL). The combined extracts were evaporated to dryness, and crude product was purified by flash chromatography (Biotage®, 4:1 hexanes/EtOAc) to yield methyl N,2-dimethyl-N-[(4′-nitrobiphenyl-4-yl)carbonyl]alaninate as an off-white solid (1.29 g, 94%). 1H NMR (400 MHz, DMSO-d6) δ 1.47 (s, 6H), 2.93 (s, 3H), 3.58 (s, 3H), 7.52 (d, 2H), 7.84 (d, 2H), 7.98 (d, 2H), 8.30 (d, 2H); LC-MS m/z 356.9 (MH+), retention time 2.98 minutes.

Workup

  1. customAs shown in Reaction Scheme 11
  2. stirringthe reaction mixture was stirred overnight at rt
  3. extractionthe mixture was extracted with ethyl acetate (2×10 mL)
  4. customThe combined extracts were evaporated to dryness, and crude product
  5. customwas purified by flash chromatography (Biotage®, 4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-fafad4ea661e4fadb373306426d8c04a
Source dataset
uspto-grants-2010_07
Patent number
US07759376B2

Reaction notes

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