Trifluoromethylsulfonamide → 1-[2-(3,5-Dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(2-oxo-2-trifluoromethanesulfonylamino-ethyl)-amide

HRID 408605Notes

Reaction equation

HRID 408605 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]([CH2:26][C:27](O)=[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.CCN=C=NCCCN(C)C.Cl.[F:44][C:45]([F:51])([F:50])[S:46]([NH2:49])(=[O:48])=[O:47]>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]([CH2:26][C:27](=[O:28])[NH:49][S:46]([C:45]([F:51])([F:50])[F:44])(=[O:48])=[O:47])[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

Participants

6

Reactant 3

HCID 79001TrifluoromethylsulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70558376((4-Chloro-benzyl)-{1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carbonyl}-amino)-acetic acid

Product 1

HCID 867020261-[2-(3,5-Dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(2-oxo-2-trifluoromethanesulfonylamino-ethyl)-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of compound 49 ((4-chloro-benzyl)-{1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carbonyl}-amino)-acetic acid (1 eq.) in DMF was added EDC.HCl (1.3 eq.), DMAP (1.3 eq.) and trifluoromethanesulfonamide (1.3 eq.). The reaction was stirred for 15 h at 20° C. The crude was concentrated under reduced pressure then partitioned between water and EtOAc. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by preparative LCMS to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(2-oxo-2-trifluoromethanesulfonylamino-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 preparative LCMS

Sources & evidence

ORD record
ord-77c7fc73c3224c8a94bd7c087b0b6b7b
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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