Phenylethanolamine → N-hydroxy-4-[3-(2-hydroxy-2-phenyl-ethyl)-ureido]-butyramide

HRID 563980Notes

Reaction equation

HRID 563980 reaction equation
CN(C)C1C=CC(CN[C:9](=[O:18])[NH:10][CH2:11][CH2:12][CH2:13][C:14]([NH:16][OH:17])=[O:15])=CC=1.[NH2:22][CH2:23][CH:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[OH:25]>>[OH:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][NH:10][C:9]([NH:22][CH2:23][CH:24]([OH:25])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:18]

Participants

3

Reactant 2

HCID 1000PhenylethanolamineHCID 575981614-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramide

Product 1

HCID 57598156N-hydroxy-4-[3-(2-hydroxy-2-phenyl-ethyl)-ureido]-butyramide

Procedure

Compound 15 was prepared using the methodology described for the preparation of compound 2, by substituting 4-dimethylaminobenzylamine dihydrochloride with 2-amino-1-phenyl-ethanol. 1H NMR (CD3OD) δ 7.42-7.24 (m, 5H), 4.73 (dd, J=7.8, 4.2 Hz, 1H), 3.43 (dd, J=13.8, 4.2 Hz, 1H), 3.26 (dd, J=13.8, 7.8 Hz, 1H), 3.14 (t, J=6.9 Hz, 2H), 2.12 (t, J=7.2 Hz, 2H), 1.76 (m, 2H). 13C NMR (CD3OD) δ 172.7, 161.5, 144.2, 129.5, 128.7, 127.3, 74.6, 48.1, 39.4, 30.6, 27.0.

Sources & evidence

ORD record
ord-e43fee0da87d4abfabfe52e86e187c72
Source dataset
uspto-grants-2011_11
Patent number
US08067600B2

Reaction notes

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