7-Amino-heptanoic acid benzyl ester toluene-4-sulfonic acid → 7-[3-(4-Dimethylamino-benzyl)-ureido]-heptanoic acid

HRID 404199Notes

Reaction equation

HRID 404199 reaction equation
[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9](=[O:18])[NH:10][CH2:11][CH2:12][CH2:13][C:14](NO)=O)=[CH:5][CH:4]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O:40][C:41](=[O:49])[CH2:42][CH2:43]CCCCN)C1C=CC=CC=1>>[CH3:1][N:2]([CH3:21])[C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9](=[O:18])[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:43][CH2:42][C:41]([OH:49])=[O:40])=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 184392197-Amino-heptanoic acid benzyl ester toluene-4-sulfonic acidHCID 575981614-[3-(4-Dimethylamino-benzyl)-ureido]-N-hydroxy-butyramide

Product 1

HCID 670070697-[3-(4-Dimethylamino-benzyl)-ureido]-heptanoic acid

Procedure

Compound 5 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 7-amino-heptanoic acid benzyl ester toluene-4-sulfonic acid. 1H NMR (300 MHz, DMSO-d6) δ (ppm) 10.33 (br, s, 1H), 8.66 (br s, 1H), 7.05 (d, J=8.7 Hz, 2H), 6.67 (d, J=8.7 Hz, 2H), 6.04 (t, J=5.7 Hz, 1H), 5.79 (t, J=5.7 Hz, 1H), 4.05 (d, J=6.0 Hz, 2H), 2.97 (dt, J=6.6, 6.6 Hz, 2H), 2.84 (s, 6H), 1.93 (t, J=7.5 Hz, 2H), 1.47 (m, 2H), 1.34 (m, 2H), 1.22 (m, 4H)

Sources & evidence

ORD record
ord-4b1e53c4b92d40749537a584c0b903bc
Source dataset
uspto-grants-2014_06
Patent number
US08748463B2

Reaction notes

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