Triphosgene → HCID 178424981, compound

HRID 408606Notes

Reaction equation

HRID 408606 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]([CH2:26][CH2:27][C:28](=[NH:31])[NH:29][OH:30])[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:35](Cl)([O:37]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][CH2:27][C:28]2[N:31]=[C:35]([OH:37])[O: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:32][CH:33]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 178424982HCID 178424982, compound

Product 1

HCID 178424981HCID 178424981, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-[2-(N-hydroxycarbamimidoyl)-ethyl]-amide (1 eq.) in dioxane was added triphosgene (1.7 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 heptane/EtOAc/DCM/MeOH: 50/50/0/0 to 50/50/90/10) to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-[2-(5-hydroxy-[1,2,4]oxadiazol-3-yl)-ethyl]-amide.

Workup

  1. concentrationThe crude was concentrated under reduced pressure
  2. customthen partitioned between water and EtOAc
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc/DCM/MeOH: 50/50/0/0 to 50/50/90/10)

Sources & evidence

ORD record
ord-3581e767da944108bc14402bbce66ab8
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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