Isopropylamine → 5-Isopropylamino-4-hydroxypentanoic acid

HRID 1995685Notes

Reaction equation

[OH:1][CH:2]([CH2:8]Cl)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].ClCC(O)C(O)=O.[CH:17]([NH2:20])([CH3:19])[CH3:18].COC1C=C(C=CC=1OC)CCN>>[CH:17]([NH:20][CH2:8][CH:2]([OH:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])([CH3:19])[CH3:18]

Participants

Reactant 4

HCID 6363Isopropylamine

HCID 8421Homoveratrylamine

HCID 92899Chlorolactic acid

HCID 202406544-Hydroxy-5-chloropentanoic acid

Product 1

HCID 202406505-Isopropylamino-4-hydroxypentanoic acid

Procedure

The procedure is repeated in all essential details, except 4-hydroxy-5-chloropentanoic acid is substituted for β-chlorolactic acid and isopropylamine is substituted for 3,4-dimethoxyphenethylamine to produce the intermediate 5-isopropylamino-4-hydroxypentanoic acid. The hydroxy and amino groups are protected as described in Example I. The resulting acid is reacted with 1-naphthol instead of phenol and the protecting groups are removed as in Example I. The resulting compound should be a short acting β-blocker.

Sources & evidence

ORD record: ord-6f2755b386124df8aee285afa4146092
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04405642

Reaction notes

Loading…