Hydrochloric Acid → HCID 715869, compound

HRID 898097Notes

Reaction equation

HRID 898097 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([C@@H:8]([CH2:10][C:11]([OH:13])=[O:12])[NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[Na+].[C:18](OC(=O)C)(=[O:20])[CH3:19].Cl>O>[C:18]([NH:9][C@H:8]([CH2:10][C:11]([OH:13])=[O:12])[C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium Hydroxide2×HCID 1381949(3R)-3-Amino-3-(4-nitrophenyl)propanoic acid

Product 1

HCID 715869HCID 715869, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

p-Nitro-β-phenylalanine (10.0 g, 48 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., 10.7 ml of acetic anhydride (105 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 1.5 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 11.6 g of acetyl-p-nitro-β-phenylalanine at a yield of 96.9%.

Workup

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

Sources & evidence

ORD record
ord-d93e525489a04c64af5d128c8b79cc36
Source dataset
uspto-grants-2008_04
Patent number
US07351571B2

Reaction notes

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