Pyridine → HCID 22951554, compound

HRID 276735Notes

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:26]=[CH:25][N:24]([CH2:27][CH2:28][CH2:29][C@H:30]([NH:34][C:35](=[O:61])[C@H:36]([CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([CH3:60])[CH:55]=2)[NH:37][C:38](=[O:52])[CH:39]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:31]([NH2:33])=O)[N:23]=1)=[O:21]>CCOC(C)=O>[CH3:18][O:19][C:20]([C:22]1[CH:26]=[CH:25][N:24]([CH2:27][CH2:28][CH2:29][C@H:30]([NH:34][C:35](=[O:61])[C@H:36]([CH2:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([CH3:60])[CH:55]=2)[NH:37][C:38](=[O:52])[CH:39]([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[C:31]#[N:33])[N:23]=1)=[O:21]

Participants

Conditions

Temperature: 0 °C

Procedure

Oxalyl chloride (0.082 mL, 0.94 mmol) is added dropwise to DMF (20 mL), and the resulting solution is cooled to 0° C. After the solution becomes clear, pyridine (0.15 mL, 1.88 mmol) is added, followed by N-[4-(3-methoxycarbonyl-1H-pyrazol-1-yl)-1(S)-(aminocarbonyl)butyl]-3-methyl-Nα-(2,2-diphenyl-acetyl)-L-phenylalaninamide (0.28 g, 0.47 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, 66% EtOAc/hexane) to yield N-[4-(3-methoxycarbonyl-1H-pyrazol-1-yl)-1(S)-cyanobutyl]-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, 66% EtOAc/hexane)

Sources & evidence

ORD record: ord-6328168959d742eca8c93cc22baa1857
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353017B1

Reaction notes

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