Pyridine → HCID 22951550, compound
Reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7]N(C=O)C.N1C=CC=[CH:14][CH:13]=1.[CH3:18][C:19]1[CH:20]=[C:21]([CH:59]=[CH:60][CH:61]=1)[CH2:22][C@@H:23]([C:40]([NH:42][C:43](=O)[C@H:44](COCC1OC(C(OC)=O)=CC=1)[NH2:45])=[O:41])[NH:24][C:25](=[O:39])[CH:26]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[CH2:63][O:64][C:65]([CH3:67])=[O:66]>>[CH3:63][O:64][C:65]([C:67]1[O:3][C:2]([CH2:1][O:5][CH2:7][C@@H:43]([NH:42][C:40](=[O:41])[C@H:23]([CH2:22][C:21]2[CH:59]=[CH:60][CH:61]=[C:19]([CH3:18])[CH:20]=2)[NH:24][C:25](=[O:39])[CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:44]#[N:45])=[CH:14][CH:13]=1)=[O:66]Participants
Conditions
- Temperature
- 0 °C
Procedure
Oxalyl chloride (0.046 mL, 0.36 mmol) is added dropwise to DMF (5 mL), and the resulting solution is cooled to 0° C. After the solution is clear, pyridine (0.032 mL, 0.40 mmol) is added, followed by N-[3-methyl-N-(2,2-diphenylacetyl)-L-phenylalanyl]-O-[[5-(methoxycarbonyl)-fur-2-yl]-methyl]-L-serinamide (0.20 g, 0.33 mmol), in one portion. The yellow reaction solution is stirred at 0° C. for 1.5 hours, after which time it is diluted with EtOAc (50 mL), and washed with saturated NaHCO3 (1×50 mL), saturated LiCl (1×50 mL), dried over MgSO4, and evaporated. The residue is chromatographed (silica, 40% EtOAc/hexane) to yield N-[2-[(5-(methoxycarbonyl)-fur-2-yl)-methoxy]-1(S)-cyanoethyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide as a white solid.
Workup
- washwashed with saturated NaHCO3 (1×50 mL), saturated LiCl (1×50 mL)
- dry with materialdried over MgSO4
- customevaporated
- customThe residue is chromatographed (silica, 40% EtOAc/hexane)
Sources & evidence
- ORD record
- ord-1f7993d434744557b591baa5f66dd53a
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06353017B1
Reaction notes
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