Bromoacetone → tert-butyl [(1S)-1-methyl-2-({6-[6-(2-oxopropoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)ethyl]carbamate

HRID 1026262Notes

Reaction equation

HRID 1026262 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]2[N:6]=[C:7]([C:9]3[N:14]=[CH:13][C:12]([O:15][CH2:16][C@@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH3:18])=[CH:11][CH:10]=3)[O:8][C:4]=2[CH:3]=1.Br[CH2:30][C:31](=[O:33])[CH3:32]>>[CH3:18][C@H:17]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[CH2:16][O:15][C:12]1[CH:13]=[N:14][C:9]([C:7]2[O:8][C:4]3[CH:3]=[C:2]([O:1][CH2:30][C:31](=[O:33])[CH3:32])[CH:28]=[CH:27][C:5]=3[N:6]=2)=[CH:10][CH:11]=1

Participants

3

Reactant 2

HCID 11715BromoacetoneHCID 136372364tert-butyl [(1S)-2-{[6-(6-hydroxy-1,3-benzoxazol-2-yl)pyridin-3-yl]oxy}-1-methylethyl]carbamate

Product 1

HCID 86666284tert-butyl [(1S)-1-methyl-2-({6-[6-(2-oxopropoxy)-1,3-benzoxazol-2-yl]pyridin-3-yl}oxy)ethyl]carbamate

Procedure

Using tert-butyl [(1S)-2-{[6-(6-hydroxy-1,3-benzoxazol-2-yl)pyridin-3-yl]oxy}-1-methylethyl]carbamate and 1-bromopropan-2-one, and in the same manner as in Example 2, step E, the title compound was obtained.

Sources & evidence

ORD record
ord-868f10d4ace447838af56d13beac1c15
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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