Triphosgene → HCID 178424979, compound

HRID 408607Notes

Reaction equation

[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]([CH2:26][C:27]([NH:29][NH2:30])=[O:28])[C:8]([C:10]2([CH3:25])[CH2:13][CH2:12][N:11]2[C:14](=[O:24])[CH2:15][C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([CH3:23])[CH:17]=2)=[O:9])=[CH:4][CH:3]=1.Cl[C:34](Cl)([O:36]C(=O)OC(Cl)(Cl)Cl)Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([CH2:26][C:27]2[O:28][C:34]([OH:36])=[N:30][N:29]=2)[C:8]([C:10]2([CH3:25])[CH2:13][CH2:12][N:11]2[C:14](=[O:24])[CH2:15][C:16]2[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=2)=[O:9])=[CH:31][CH:32]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of the Intermediate obtained in step b above (1 eq.) in dioxane was added triphosgene (1.5 eq.) under nitrogen. The reaction was stirred at 20° C. for 15 h. The crude was concentrated under reduced pressure then partitioned between water and EtOAc. The layers were separated, the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with Hept/EtOAc/DCM/MeOH: 50/50/0/0 to 50/50/95/5) to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(5-hydroxy-[1,3,4]oxadiazol-2-ylmethyl)-amide.

Workup

concentrationThe crude was concentrated under reduced pressure
customthen partitioned between water and EtOAc
customThe layers were separated
dry with materialthe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude was purified by chromatography on silica gel (elution with Hept/EtOAc/DCM/MeOH: 50/50/0/0 to 50/50/95/5)

Sources & evidence

ORD record: ord-1b659ac79f9542d8a926ff3e5d555205
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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