N-((1,1-dimethylethoxy)carbonyl)-beta-alanine → 5-[3-(1-t-Butoxyformamido)propionamido]-2-nitrobenzoic acid
Reaction equation
C(OC(=O)CCN[C:10](=[O:33])[C:11]1[CH:16]=[C:15]([NH:17][C:18](=[O:29])[CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:14]=[CH:13][C:12]=1[N+:30]([O-:32])=[O:31])(C)(C)C.C([O:39]C(NCCC(O)=O)=O)(C)(C)C.NC1C=CC([N+]([O-])=O)=C(C=1)C(O)=O>>[C:25]([O:24][C:22]([NH:21][CH2:20][CH2:19][C:18]([NH:17][C:15]1[CH:14]=[CH:13][C:12]([N+:30]([O-:32])=[O:31])=[C:11]([CH:16]=1)[C:10]([OH:33])=[O:39])=[O:29])=[O:23])([CH3:26])([CH3:27])[CH3:28]Participants
4
Procedure
For the preparation of the ester starting material, N-(t-butoxycarbonyl)-β-alanine and 5-amino-2-nitrobenzoic acid are coupled to give 5-[3-(1-t-butoxyformamido)propionamido]-2-nitrobenzoic acid, MS: 354 (17, M+H), and the latter is reacted with β-alanine t-butyl ester.
Sources & evidence
- ORD record
- ord-101212eaaf064c6bb391393669452fad
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05039805
Reaction notes
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