Hydrochloric Acid → Melphalan hydrochloride

HRID 1411208Notes

Reaction equation

HRID 1411208 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[CH:16]=[CH:15][C:8]([CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:7][CH:6]=1.Cl>C1(C)C=CC=CC=1>[ClH:1].[Cl:1][CH2:2][CH2:3][N:4]([CH2:17][CH2:18][Cl:19])[C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 460612Melphalan

Product 1

HCID 9927978Melphalan hydrochloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[Bis(2-chloroethyl)-amino]-L-phenylalanine (V) obtained in Example 2 was treated with concentrated hydrochloric acid (80 ml) at 25° C. to 30° C. and stirred at the same temperature for 15-20 hours. Toluene (1060 ml) was added and the resulting mixture was concentrated under reduced pressure till the moisture content of the residue was about 5%. Isopropyl alcohol (765 ml) was added to the resulting residue and stirred at 0° C. to 5° C. for 2-4 hours. 4-[Bis(2-chloroethyl)-amino]-L-phenylalanine hydrochloride thus obtained was filtered, washed with isopropyl alcohol (340 ml) and dried under reduced pressure at 45° C. to 50° C.

Workup

  1. concentrationthe resulting mixture was concentrated under reduced pressure till the moisture content of the residue
  2. additionIsopropyl alcohol (765 ml) was added to the resulting residue
  3. stirringstirred at 0° C. to 5° C. for 2-4 hours

Sources & evidence

ORD record
ord-2380449a0b9e40f6a98e7f9bd9788b01
Source dataset
uspto-grants-2014_12
Patent number
US08921596B2

Reaction notes

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