Hydrochloric Acid → 3,4-Methylenedioxyphenylalanyl chloride hydrochloride

HRID 329171Notes

Reaction equation

[CH2:1]1[O:15][C:14]2[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9](O)=[O:10])[NH2:8])=[CH:4][C:3]=2[O:2]1.Cl.P(Cl)(Cl)(Cl)(Cl)[Cl:18].Cl.C1(NCC([Cl:34])=O)C=CC=CC=1>>[ClH:18].[CH2:1]1[O:15][C:14]2[CH:13]=[CH:12][C:5]([CH2:6][C@@H:7]([C:9]([Cl:34])=[O:10])[NH2:8])=[CH:4][C:3]=2[O:2]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 24819Phosphorus pentachloride

HCID 12918717(S)-2-Amino-3-(benzo[D][1,3]dioxol-5-YL)propanoic acid

HCID 13140662N-Phenylglycyl chloride--hydrogen chloride (1/1)

Product 1

HCID 867342163,4-Methylenedioxyphenylalanyl chloride hydrochloride

Procedure

The compound 3,4-methylenedioxyphenylalanine, Ber., 59, 2952 (1926), is treated with hydrogen chloride and phosphorous pentachloride in accordance with the procedure described by Hartcastle et al., J. Org. Chem., 31, 897 (1966) for the preparation of phenylglycyl chloride hydrochloride to yield 3,4-methylenedioxyphenylalanyl chloride hydrochloride.

Sources & evidence

ORD record: ord-2c6906adf7194110b7100c74188569f5
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04020060

Reaction notes

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