Hydrochloric Acid → HCID 58018315, compound

HRID 557452Notes

Reaction equation

HRID 557452 reaction equation
[OH-].[Na+].[I:3][C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1.[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:18]=1[C:19](Cl)=[O:20].Cl>CC(C)=O.O>[Cl:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[C:18]=1[C:19]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([I:3])=[CH:15][CH:14]=1)=[O:20]

Participants

7

Conditions

Temperature
10 °C

Procedure

Water (21 mL), acetone (9.80 mL) and a 6M sodium hydroxide aqueous solution (5.20 mL) were added to 7.50 g of 4-iodo-L-phenylalanine and the resulting mixture was stirred at 10° C. to thus give a uniform solution. To this solution, there were alternatively added 4.05 mL of 2,6-dichlorobenzoyl chloride and 4.50 mL of a 6M sodium hydroxide aqueous solution while taking care to maintain the pH value of not less than 13 and the temperature of not higher than 15° C. After confirming the completion of the reaction, 6.50 mL of a 6M hydrochloric acid aqueous solution was added to the reaction system to thus precipitate the desired product. The solid thus separated was isolated through filtration under reduced pressure, washed with 15 mL of water and dried at 70° C. for 4 hours under reduced pressure to thus give 12.42 g of the intended product.

Workup

  1. customto thus give a uniform solution
  2. temperatureto maintain the pH value of not less than 13
  3. customhigher than 15° C
  4. additionwas added to the reaction system
  5. customto thus precipitate the desired product
  6. customThe solid thus separated
  7. customwas isolated through filtration under reduced pressure
  8. washwashed with 15 mL of water
  9. dry with materialdried at 70° C. for 4 hours under reduced pressure to thus give 12.42 g of the intended product

Sources & evidence

ORD record
ord-111a426690064f29aeecdaf0dae6da16
Source dataset
uspto-grants-2011_11
Patent number
US08058432B2

Reaction notes

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