Diisopropylethylamine → HCID 86752013, compound

HRID 727725Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][S:8][C@@H:9]2[CH2:13][N:12]([CH3:14])[C@H:11]([C:15]([OH:17])=O)[CH2:10]2)=[CH:5][CH:4]=1.Cl.Cl.N[CH:23]1[CH2:26][NH:25][CH2:24]1.C([N:30](C(C)C)CC)(C)C>C(#N)C.CO>[NH2:30][CH:10]1[CH:9]([S:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=2)[CH2:13][N:12]([CH3:14])[CH:11]1[C:15]([N:25]1[CH2:26][CH2:23][CH2:24]1)=[O:17]

Participants

Conditions

Temperature: 40 °C

Procedure

1.62 g of (2S,4S)-4-(4-methoxybenzylthio)-1-methyl-2-pyrrolidinecarboxylic acid were suspended in 20 ml of dry acetonitrile, and 1.02 g of N,N'-carbonyldiimidazole were added to the suspension, after which the mixture was stirred at 40° C. for 45 minutes. A solution of 1.00 g of 3-aminoazetidine dihydrochloride and 2.40 ml of diisopropylethylamine in 10 ml of methanol was added dropwise to the mixture, whilst ice-cooling, and the mixture was stirred at the same temperature for 90 minutes. At the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure. The resulting residue was subjected to reverse phase column chromatography (Cosmosil 75C18 -PREP, manufactured by Nacalai Tesque, 145 g) to give 1.21 g of the title compound, as a colorless oil, from the fraction obtained by solution with 30% by volume aqueous acetonitrile.

Workup

temperaturecooling
stirringthe mixture was stirred at the same temperature for 90 minutes
concentrationAt the end of this time, the reaction mixture was concentrated by evaporation under reduced pressure

Sources & evidence

ORD record: ord-b7e0bcf4ea764c05a5d92bba3bd299ac
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05712267

Reaction notes

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