Hydrogen Bromide → HCID 53400894, compound

HRID 1450686Notes

Reaction equation

HRID 1450686 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:13]=O.[BrH:15]>>[BrH:15].[CH2:13]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]([C:10]([OH:12])=[O:11])[NH:1]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 712FormaldehydeHCID 6140L-Phenylalanine

Product 1

HCID 53400894HCID 53400894, compoundYield 86.4%

Conditions

Temperature
65 °C

Procedure

To 10 g of L-phenylalanine suspended in 108 ml of 47% hydrobromic acid, 23 ml of 37% formalin aqueous solution was added dropwise. The reaction mixture was stirred at 65° C. for 7 hours, and subjected to crystallization under ice cooling for 3 hours. The precipitate was filtered off, and dried at 55° C. under reduced pressure to obtain 13.5 g of Compound 2 (yield 86.4%, optical purity 97% ee).

Workup

  1. customsubjected to crystallization under ice cooling for 3 hours
  2. filtrationThe precipitate was filtered off
  3. customdried at 55° C. under reduced pressure

Sources & evidence

ORD record
ord-a7fed4072ca346208837b4b8903f952e
Source dataset
uspto-grants-1997_02
Patent number
US05602255

Reaction notes

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