Ethanesulfonyl chloride → tert-butyl (3R)-6-cyclohexyl-3-(3-{[(ethylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

HRID 2084447Notes

Reaction equation

HRID 2084447 reaction equation
[NH2:1][CH2:2][C:3]1[N:7]=[C:6]([C@H:8]([CH2:17][CH2:18][CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[O:5][N:4]=1.[CH2:26]([S:28](Cl)(=[O:30])=[O:29])[CH3:27]>>[CH:20]1([CH2:19][CH2:18][CH2:17][C@@H:8]([C:6]2[O:5][N:4]=[C:3]([CH2:2][NH:1][S:28]([CH2:26][CH3:27])(=[O:30])=[O:29])[N:7]=2)[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:16])[CH3:14])=[O:11])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

3

Reactant 2

HCID 11667Ethanesulfonyl chlorideHCID 16747946tert-butyl(3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate

Product 1

HCID 16748328tert-butyl (3R)-6-cyclohexyl-3-(3-{[(ethylsulfonyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

Procedure

Method the same as for Preparation 6 using tert-butyl (3R)-3-[3-(aminomethyl)-1,2,4-oxadiazol-5-yl]-6-cyclohexylhexanoate (preparation 18) (200 mg, 0.57 mmol) and ethanesulphonylchloride (54 μl, 0.57 mmol) as starting materials. The reaction was carried out at 0° C.

Workup

  1. customwas carried out at 0° C.

Sources & evidence

ORD record
ord-4dc5ad9e36044e298082c7c636fa1386
Source dataset
uspto-grants-2004_04
Patent number
US06716861B2

Reaction notes

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