Pyridine → HCID 10886424, compound

HRID 276737Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CN(C=O)C.N1C=CC=CC=1.[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][C@H:31]([NH:35][C:36](=[O:62])[C@H:37]([CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[C:57]([CH3:61])[CH:56]=2)[NH:38][C:39](=[O:53])[CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:32]([NH2:34])=O)[CH:25]=[CH:26][CH:27]=1)=[O:21]>CCOC(C)=O>[CH3:18][O:19][C:20]([C:22]1[CH:23]=[C:24]([CH2:28][CH2:29][CH2:30][C@H:31]([NH:35][C:36](=[O:62])[C@H:37]([CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[C:57]([CH3:61])[CH:56]=2)[NH:38][C:39](=[O:53])[CH:40]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:47]2[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=2)[C:32]#[N:34])[CH:25]=[CH:26][CH:27]=1)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Oxalyl chloride (0.12 mL, 1.39 mmol) is added dropwise to DMF (10 mL), and the resulting solution is cooled to 0° C. After the solution is clear, pyridine (0.22 mL, 2.78 mmol) is added, followed by N-[4-(3-methoxycarbonylphenyl)-1(S)-(aminocarbonyl)butyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide (0.42 g, 0.70 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 aqueous NaHCO3 solution (1×50 mL), saturated aqueous LiCl solution (1×50 mL), dried over MgSO4, and evaporated. The residue is chromatographed to yield N-[4-(3-methoxycarbonyl-phenyl)-1(S)-cyanobutyl]-3-methyl-Nα-(2,2-diphenylacetyl)-L-phenylalaninamide, as a yellow solid.

Workup

washwashed with saturated aqueous NaHCO3 solution (1×50 mL), saturated aqueous LiCl solution (1×50 mL)
dry with materialdried over MgSO4
customevaporated
customThe residue is chromatographed

Sources & evidence

ORD record: ord-602d27d613734be29cfbc40f95bacd9c
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353017B1

Reaction notes

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