Phenylethanolamine → N-hydroxy-3-[3-(2-hydroxy-2-phenyl-ethyl)-ureido]-propionamide

HRID 404207Notes

Reaction equation

HRID 404207 reaction equation
CN(C)C1C=CC(CNC(=O)NC[CH2:12][CH2:13][C:14]([NH:16][OH:17])=[O:15])=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O[C:41](=[O:45])CCN)C1C=CC=CC=1.Cl.Cl.C[N:49](C)C1C=CC(CN)=CC=1.[NH2:59][CH2:60][CH:61]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)[OH:62]>>[OH:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][NH:49][C:41]([NH:59][CH2:60][CH:61]([OH:62])[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1)=[O:45]

Participants

5

Reactant 4

HCID 1000PhenylethanolamineHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochlorideHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)HCID 575981614-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramide

Product 1

HCID 57598155N-hydroxy-3-[3-(2-hydroxy-2-phenyl-ethyl)-ureido]-propionamide

Procedure

Compound 14 was prepared using the methodology described for the preparation of Compound 2, by substituting 4-amino-butyric acid benzyl ester toluene-4-sulfonic acid with 3-amino-propionic acid benzyl ester toluene-4-sulfonic acid and 4-dimethylaminobenzylamine dihydrochloride with 2-amino-1-phenyl-ethanol. 1H NMR (CD3OD) δ 7.40-7.22 (m, 5H), 4.69 (dd, J=7.8, 4.2 Hz, 1H), 3.41-3.34 (m, 3H), 3.22 (dd, J=13.8, 7.8 Hz, 1H), 2.25 (t, J=6.9 Hz, 2H). 13C NMR (CD3OD) δ 171.1, 161.3, 144.2, 129.5, 128.7, 127.3, 74.6, 48.9, 37.5, 34.7.

Sources & evidence

ORD record
ord-dedb5cf989484f619f2f87e0ec309baf
Source dataset
uspto-grants-2014_06
Patent number
US08748463B2

Reaction notes

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