Tetrahydrofuran → HCID 70556780, compound

HRID 408598Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([N:12]1[CH2:15][CH2:14][C:13]1([CH3:19])[C:16]([OH:18])=O)=[O:11].C1COCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][NH2:53])=[CH:50][CH:49]=1>CN(C=O)C>[CH3:47][C:48]1[CH:55]=[CH:54][C:51]([CH2:52][NH:53][C:16]([C:13]2([CH3:19])[CH2:14][CH2:15][N:12]2[C:10](=[O:11])[CH2:9][C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])=[O:18])=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 1-[2-(2,4-dichloro-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid, Intermediate 120 (1 eq.) in either THF or DMF was added TEA (4 eq.) and TBTU (2 eq.). The reaction was stirred at 20° C. for 30 min, then 4-methyl-benzylamine (1.5 eq.) was added. The reaction was stirred at 20° C. for 72 h. The crude was concentrated under reduced pressure then partitioned between water and EtOAc. The organic layer was washed twice with water, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by preparative LCMS to afford 1-[2-(2,4-dichloro-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid 4-methyl-benzylamide.

Workup

stirringThe reaction was stirred at 20° C. for 72 h
concentrationThe crude was concentrated under reduced pressure
customthen partitioned between water and EtOAc
washThe organic layer was washed twice with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude was purified by preparative LCMS

Sources & evidence

ORD record: ord-fe0a5ae2421744cb9eff4315e428f712
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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