Hydrochloric Acid → HCID 25417233, compound

HRID 1172044Notes

Reaction equation

HRID 1172044 reaction equation
[Br:1][C:2]1[CH:13]=[CH:12][C:5]([C@@H:6]([CH2:8][C:9]([OH:11])=[O:10])[NH2:7])=[CH:4][CH:3]=1.[OH-].[Na+].[C:16](OC(=O)C)(=[O:18])[CH3:17].Cl>O>[C:16]([NH:7][C@H:6]([CH2:8][C:9]([OH:11])=[O:10])[C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:13][CH:12]=1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 724054(r)-3-(p-Bromophenyl)-beta-alanine

Product 1

HCID 25417233HCID 25417233, compoundYield 102.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

p-Bromo-β-phenylalanine (10.0 g, 41 mmol) was mixed with 40 ml of water and adjusted to pH 14 with 25% sodium hydroxide aqueous solution. After being cooled to 5° C., 8.5 ml of acetic anhydride (90 mmol) and 25% sodium hydroxide aqueous solution were simultaneously dropped into the mixture to keep it at a pH range of 11.5˜12 and the resulting mixture was stirred for 3 hours at a room temperature. After the mixture was adjusted to pH 2 with conc. HCl and stirred for one hour, the resulting precipitated crystal was filtered and dried under reduced pressure to give quantitatively 12.0 g of acetyl-p-bromo-β-phenylalanine.

Workup

  1. stirringstirred for one hour
  2. customthe resulting precipitated crystal
  3. filtrationwas filtered
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-ecdb8b282c9b4a18b0ab8f6b25fbb478
Source dataset
uspto-grants-2010_11
Patent number
US07833760B2

Reaction notes

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