Methanol → methyl N-(2,6-dichlorobenzoyl)-4-iodo-L-phenylalaninate

HRID 1037817Notes

Reaction equation

HRID 1037817 reaction equation
[CH3:1]O.S(=O)(=O)(O)O.[Cl:8][C:9]1[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:10]=1[C:11]([NH:13][C@H:14]([C:23]([OH:25])=[O:24])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([I:22])=[CH:18][CH:17]=1)=[O:12]>O>[CH3:1][O:24][C:23](=[O:25])[C@H:14]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([I:22])=[CH:20][CH:21]=1)[NH:13][C:11](=[O:12])[C:10]1[C:9]([Cl:8])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:30]

Participants

5

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 58018315HCID 58018315, compound

Product 1

HCID 59665509methyl N-(2,6-dichlorobenzoyl)-4-iodo-L-phenylalaninate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

Methanol (40 mL) and 0.98 mL of concentrated sulfuric acid were added to 8.0 g of Nα-(2,6-dichlorobenzoyl)-4-iodo-L-phenylalanine and the reaction was carried out for 4 hours while heating the reaction system at 40° C. After confirming the completion of the reaction, the reaction system was cooled to 10° C. and 20 mL of water was dropwise added to separate out solid. The solid thus precipitated was isolated through filtration under reduced pressure, washed with 40 mL of water and then dried at 70° C. under reduced pressure to thus give 7.40 g of the desired product as a solid.

Workup

  1. customthe completion of the reaction
  2. temperaturethe reaction system was cooled to 10° C.
  3. customto separate out solid
  4. customThe solid thus precipitated
  5. customwas isolated through filtration under reduced pressure
  6. washwashed with 40 mL of water
  7. dry with materialdried at 70° C. under reduced pressure to thus give 7.40 g of the desired product as a solid

Sources & evidence

ORD record
ord-b6580e0b9fdd434fad8d5686965a6b2a
Source dataset
uspto-grants-2013_10
Patent number
US08546610B2

Reaction notes

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