Dimethylformamide → HCID 11963228, compound
Reaction equation
[CH3:1][N:2]([C:7]1[CH:8]=[C:9]([CH:13]=[C:14]([C:16](=[O:26])[NH:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])[CH:15]=1)[C:10](O)=[O:11])[S:3]([CH3:6])(=[O:5])=[O:4].[OH2:27].ON1[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=2N=N1.C([N:41]([CH:44]([CH3:46])C)[CH2:42][CH3:43])(C)C.CN([CH:50]=[O:51])C>C(Cl)Cl>[OH:27][CH:46]([CH2:44][NH:41][CH2:42][C:43]1[CH:16]=[CH:14][CH:13]=[C:9]([O:51][CH3:50])[CH:8]=1)[CH:7]([NH:2][C:10](=[O:11])[C:9]1[CH:8]=[C:7]([N:2]([CH3:1])[S:3]([CH3:6])(=[O:5])=[O:4])[CH:15]=[C:14]([C:16]([NH:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH3:19])=[O:26])[CH:13]=1)[CH2:15][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
Tert-butyl 3-hydroxy-4-(3-methoxybenzylamino)-1-phenylbutan-2-ylcarbamate was obtained in a single step by the ring opening reaction of tert-butyl-(1-oxiranyl-2-phenylethyl)-carbamate with 3-methoxybenzylamine under reflux condition in 2-propanol. Deprotection of Boc group by treatment of TFA in CH2Cl2 or methanolic HCl provided 3-amino-1-(3-methoxybenzylamino)-4-phenylbutan-2-ol, which was directly exposed to peptide coupling reaction with 3-(N-methylmethylsulfonamido)-5-(1-phenylethylcarbamoyl)benzoic acid in presence of N-ethyl-N′-(dimethylaminopropyl)carbodiimde hydrochloride (EDC), 1-hydroxybenzotriazole hydrate and diisopropylethylamine in a mixture of DMF and CH2Cl2 to afford N1-(3-hydroxy-4-(3-methoxybenzylamino)-1-phenylbutan-2-yl)-5-(N-methylmethylsulfonamido)-N3-(1-phenylethyl)isophthalamide.
Sources & evidence
- ORD record
- ord-86a83da1fa074becaad5021827bd0a08
- Source dataset
- uspto-grants-2009_03
- Patent number
- US07504420B2
Reaction notes
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