2,4,6-Trimethylpyridine → 3-{[5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carbonyl]-amino}-3-phenyl-propionic Acid Tert-butyl Ester
Reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][C:13]([C:15]1[S:19][C:18]([C:20]([OH:22])=O)=[CH:17][CH:16]=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:23]([O:27][C:28](=[O:38])[CH2:29][CH:30]([NH2:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:26])([CH3:25])[CH3:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C(C)=CC(C)=CC=1C>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[C:23]([O:27][C:28](=[O:38])[CH2:29][CH:30]([NH:37][C:20]([C:18]1[S:19][C:15]([C:13](=[O:14])[NH:12][CH2:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[CH:16][CH:17]=1)=[O:22])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]Participants
7
Reactant 4
HCID 79532,4,6-Trimethylpyridine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 14557402Tert-butyl 3-amino-3-phenylpropanoate
HCID 222852255-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carboxylic AcidProduct 1
Reagents, catalysts & solvents 2
Procedure
With continued reference to Scheme G, 5-(3-tert-Butoxycarbonylamino-propylcarbamoyl)-thiophene-2-carboxylic acid (200 mg, 0.704 mmol) was reacted with 3-Amino-3-phenyl-propionic acid tert-butyl ester (187 mg, 0.845 mmol) in 4.0 ml of anhydrous DMF using HATU (321 mg, 0.845 mmol) with 2,4,6-collidine (0.25 ml, 2.112 mmol), chromatographied on silica gel using ethyl acetate: hexane (8:2) to give 200 mg (58% yield) of the desired product as a clear semi-solid oil. 1H NMR (400 Mhz, CDCl3) 1.3 (s, 9H), 1.45 (s, 9H), 1.7 (m, 2H), 2.9 (ddd, 2H), 3.25 (m, 2H), 3.5 (q, 2H), 4.85 (bs, 1H), 5.55 (m, 1H), 7.23 (m, 1H), 7.33 (m, 4H), 7.4-7.6 (m, 4H).
Sources & evidence
- ORD record
- ord-e4ff4c47a8334334a6bbf207a556f226
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06960594B2
Reaction notes
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