Imidazole → HCID 67087069, compound

HRID 1665148Notes

Reaction equation

HRID 1665148 reaction equation
[NH2:1][C@H:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:3]([NH2:5])=[O:4].N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22]>C1COCC1>[NH2:1][C@H:2]([CH2:6][CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27])=[CH:13][CH:14]=1)[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67086706HCID 67086706, compound

Product 1

HCID 67087069HCID 67087069, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of (R)-2-Amino-5-(4-hydroxy-phenyl)-pentanoic acid amide (5 g, 24.01 mmol) in THF (250 ml) is added imidazole (4.90 g, 72 mmol), followed by tert-butyldimethylchlorosilane (3.98 g, 26.4 mmol). The resulting solution is heated at 70° C. for 4 hours and then allowed to cool to room temperature. Dilution with Et2O (200 ml) washing with water (2×100 ml) and brine (100 ml), drying MgSO4, and concentration in vacuo yields (R)-2-Amino-5-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-pentanoic acid amide; [M+H]+ 323

Workup

  1. temperatureto cool to room temperature
  2. washDilution with Et2O (200 ml) washing with water (2×100 ml) and brine (100 ml)
  3. customdrying
  4. concentrationMgSO4, and concentration in vacuo

Sources & evidence

ORD record
ord-4d0d337e3051412e81bcfd9e6bc097bf
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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