Isopropyl iodide → tert-butyl [(1S)-1-methyl-2-({5-[5-(1-methylethoxy)-1,3-benzoxazol-2-yl]isoxazol-3-yl}oxy)ethyl]carbamate

HRID 1026263Notes

Reaction equation

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

Participants

Reactant 2

HCID 6362Isopropyl iodide

HCID 86666264tert-butyl [(1S)-2-{[5-(5-hydroxy-1,3-benzoxazol-2-yl)isoxazol-3-yl]oxy}-1-methylethyl]carbamate

Product 1

HCID 86666285tert-butyl [(1S)-1-methyl-2-({5-[5-(1-methylethoxy)-1,3-benzoxazol-2-yl]isoxazol-3-yl}oxy)ethyl]carbamate

Procedure

Using tert-butyl [(1S)-2-{[5-(5-hydroxy-1,3-benzoxazol-2-yl)isoxazol-3-yl]oxy}-1-methylethyl]carbamate (200 mg) and 2-iodopropane (0.106 mL), and in the same manner as in Example 2, step E, the title compound was obtained (246 mg).

Sources & evidence

ORD record: ord-022b59f9df3a4cf2b5e353434a90b675
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729102B2

Reaction notes

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