Dimethylformamide → Methyl 4-hydroxy-3-iodobenzoate

HRID 1714577Notes

Reaction equation

HRID 1714577 reaction equation
CC(OC(N[C@@H:9](CC1C=CC(C2N=C(C(N(C)OC)=O)N(C)C=2)=CC=1)[CH2:10][CH2:11][C:12]([O:14][C:15](C)(C)C)=[O:13])=O)(C)C.[I:38][CH:39]([CH3:41])[CH3:40].CCN(C(C)C)C(C)C.CN(C=[O:55])C>>[OH:55][C:40]1[CH:9]=[CH:10][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:41][C:39]=1[I:38]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6362Isopropyl iodideHCID 81531DiisopropylethylamineHCID 866047661,1-dimethylethyl (4R)-4-({[(1,1-dimethylethyl)oxy]carbonyl)amino)-5-[4-(1-methyl-2-{[methyl(methyloxy)amino]carbonyl}-1H-imidazol-4-yl)phenyl]pentanoate

Product 1

HCID 11346465Methyl 4-hydroxy-3-iodobenzoateYield 20%

Conditions

Temperature
80 °C

Procedure

To a solution of compound 1 (200 mg, 1.077 mmol) and 2-iodopropane, (322 uL, 3.23 mmol) in DMF (10 mL) was added DIEA (750 uL, 4.31 mmol). The reaction mixture was heated to 80° C. and stirred overnight. The reaction was monitored by LC/MS. After the reaction was done it was cooled to room temperature. The reaction mixture was quenched with HCl (0.5 N, 30 mL) and extracted with ethyl acetate (50 mL×3). The organic layer was dried over sodium sulfate and concentrated and dried under high vacuum. The resulting residue was purified by reverse phase chromatography using a mixture of acetonitrile and water to give compound 2 (50 mg, 20%).

Workup

  1. temperaturewas cooled to room temperature
  2. customThe reaction mixture was quenched with HCl (0.5 N, 30 mL)
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated
  6. customdried under high vacuum
  7. customThe resulting residue was purified by reverse phase chromatography
  8. additiona mixture of acetonitrile and water

Sources & evidence

ORD record
ord-e2e4cc66bc86493ba08e952ba9ad5ca2
Source dataset
uspto-grants-2010_09
Patent number
US07795448B2

Reaction notes

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