HCID 86702029, compound → HCID 68176357, compound

HRID 408609Notes

Reaction equation

[Cl:1][C:2]1[CH:45]=[CH:44][C:5]([CH2:6][N:7]([CH2:26][CH2:27][CH2:28][S:29](=[O:43])(=[O:42])[NH:30]CC2C=CC(OC)=CC=2OC)[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>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[CH:45]=[CH:44][C:5]([CH2:6][N:7]([CH2:26][CH2:27][CH2:28][S:29](=[O:43])(=[O:42])[NH2:30])[C:8]([C:10]2([CH3:25])[CH2:13][CH2:12][N:11]2[C:14](=[O:24])[CH2:15][C:16]2[CH:17]=[C:18]([CH3:23])[CH:19]=[C:20]([CH3:22])[CH:21]=2)=[O:9])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 20 °C

Procedure

1-[2-(3,5-Dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-[3-(2,4-dimethoxy-benzylsulfamoyl)-propyl]-amide, compound 168 was dissolved in TFA and stirred at 20° C. for 15 h. The crude was concentrated under reduced pressure then partitioned between water and EtOAc. The organic layer was washed twice with water, then dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc/DCM/MeOH: 1/0/0/0 then 0/1/0/0 then 50/50/95/5 then 50/50/90/10) to afford 1-[2-(3,5-dimethyl-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-(3-sulfamoyl-propyl)-amide.

Workup

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 chromatography on silica gel (
washelution with heptane/EtOAc/DCM/MeOH

Sources & evidence

ORD record: ord-4707257279ee482d96622815bd81b92f
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08759334B2

Reaction notes

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