Sodium hydride → HCID 23562817, compound

HRID 1058856Notes

Reaction equation

HRID 1058856 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[H-].[Na+].[Cl:24][C:25]1[CH:33]=[N:32][CH:31]=[C:30]([Cl:34])[C:26]=1[C:27](Cl)=[O:28].[NH4+].[Cl-]>C1COCC1>[CH3:1][O:2][C:3](=[O:21])[C@H:4]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:27](=[O:28])[C:26]2[C:25]([Cl:24])=[CH:33][N:32]=[CH:31][C:30]=2[Cl:34])=[CH:16][CH:15]=1)[NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:10])[CH3:11])=[O:7]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7019130Boc-Tyr-OMeHCID 115720223,5-Dichloropyridine-4-carbon chloride

Product 1

HCID 23562817HCID 23562817, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of N-BOC-L-tyrosine methyl ester (2.95 g, 10 mmol) in THF (10 ml) was added to a suspension of NaH (60% in oil, 11 mmol, 440 mg) in THF (30 ml) at 0°. After 10 min, a solution of 3,5-dichloroisonicotinoyl chloride (11 mml, 2.32 g) in THF (10 ml) was added and the mixture stirred at RT for 4 h. NH4Cl (aq) was added and the mixture extracted with DCM. The DCM extracts were dried (Na2SO4) and concentrated in vacuo. Recrystallisation (EtOAc/hexane) gave the title compound as white crystals (3.61 g, 77%). δH (DMSO d6) 8.89 (2H, s), 7.39 (2H, d, J 8.5 Hz), 7.32 (1H, d, J 8.2 Hz), 7.23 (2H, d, J 8.5 Hz), 4.21 (1H, m), 3.62 (3H, s), 3.05 (1H, dd, J 13.8, 4.9 Hz), 2.89 (1H, dd, J 13.8, 10.5 Hz), 1.31 (9H). m/z (ES+, 70V) 410 (M++Na).

Workup

  1. extractionthe mixture extracted with DCM
  2. dry with materialThe DCM extracts were dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customRecrystallisation (EtOAc/hexane)

Sources & evidence

ORD record
ord-d8713723b1824eccb980378ac04bf180
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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