4-Nitrophenyl chloroformate → 3-Phenyl-3-(2-{3-[3-(pyridin-2-ylamino)propyl]ureido}ethanoylamino)propionic acid
Reaction equation
[C:1]1([CH:7]([NH:12][C:13]([O:15]CC2C3C=CC=CC=3C3C2=CC=CC=3)=O)[CH2:8][C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[NH:36][CH2:37][CH2:38][CH2:39][NH:40][C:41](=[O:47])[NH:42][CH2:43]C(O)=O.Cl.Cl.N1C=CC=CC=1NCCCN.ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.NCC(OC(C)(C)C)=O>>[C:1]1([CH:7]([NH:12][C:13](=[O:15])[CH2:43][NH:42][C:41]([NH:40][CH2:39][CH2:38][CH2:37][NH:36][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=2)=[O:47])[CH2:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
6
Reactant 5
Product 1
Procedure
prepared by reaction of 3-(phenyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)propionic acid with the solid phase polystyrene A OH (Rapp, Art. No. HA 1 400 00), is reacted with {3-[3-(pyridin-2-ylamino)propyl]ureido}acetic acid (prepared analogously to Example 1 by reaction of N1-pyridin-2-ylpropane-1,3-diamine dihydrochloride with 4-nitrophenyl chloroformate and tert-butyl aminoacetate and cleavage of the ester) and cleaved off from the support, giving 3-phenyl-3-(2-{3-[3-(pyridin-2-ylamino)propyl]ureido}ethanoylamino)propionic acid.
Sources & evidence
- ORD record
- ord-c16a00d67f71484f8c01ef256f4b4494
- Source dataset
- uspto-grants-2006_11
- Patent number
- US07135587B2
Reaction notes
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