Methyl iodide → HCID 70556991, compound

HRID 408616Notes

Reaction equation

[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][N:7]([C:14]([C:16]2([CH3:31])[CH2:19][CH2:18][N:17]2[C:20](=[O:30])[NH:21][C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=2)=[O:15])[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[H-].[Na+].[CH3:36]I>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:14]([C:16]2([CH3:31])[CH2:19][CH2:18][N:17]2[C:20](=[O:30])[N:21]([C:22]2[CH:27]=[C:26]([CH3:28])[CH:25]=[C:24]([CH3:29])[CH:23]=2)[CH3:36])=[O:15])[CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:32][CH:33]=1

Participants

Conditions

Temperature: 20 °C

Procedure

To a solution of 4-{(4-chloro-benzyl)-[1-(3,5-dimethyl-phenylcarbamoyl)-2-methyl-azetidine-2-carbonyl]-amino}-butyric acid, compound 200 (1 eq.) in DMF was added NaH (3 eq.). The reaction was stirred for 1 h at 20° C., then MeI (2.5 eq.) was added. The reaction was stirred for 15 h at 20° C. The crude was partitioned between aqueous HCl (0.1N) and EtOAc. The organic layer was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by preparative LCMS to afford 4-((4-chloro-benzyl)-{1-[(3,5-dimethyl-phenyl)-methyl-carbamoyl]-2-methyl-azetidine-2-carbonyl}-amino)-butyric acid.

Workup

stirringThe reaction was stirred for 15 h at 20° C
customThe crude was partitioned between aqueous HCl (0.1N) and EtOAc
washThe organic layer was washed with water
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude was purified by preparative LCMS

Sources & evidence

ORD record: ord-7b5cd8392b2c47c2adcb3eb1d82dd581
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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