3-((Tert-butyldiphenylsilyl)oxy)azetidine → HCID 54591371, compound

HRID 1260189Notes

Reaction equation

HRID 1260189 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[CH:9][C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)=[N:7]1.[Si]([O:50][CH:51]1[CH2:54][NH:53][CH2:52]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>>[CH3:11][C:10]1[N:6]([CH2:5][C:4]2[CH:3]=[C:2]([N:53]3[CH2:54][CH:51]([OH:50])[CH2:52]3)[CH:32]=[CH:31][CH:30]=2)[N:7]=[C:8]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:22]=[CH:21][C:20]([C:23]([CH3:29])([CH3:28])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=3)[N:13]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 178425313-((Tert-butyldiphenylsilyl)oxy)azetidineHCID 58072152HCID 58072152, compound

Product 1

HCID 54591371HCID 54591371, compound

Procedure

Analogously to the process described in Example 1, 150 mg (0.297 mmol) of the compound from Example 3A and 139 mg (0.445 mmol) of the compound from Example 8A were used to obtain 68 mg (46% of theory) of the title compound. The reaction time in the first component step of the process here was 1 h. The crude product was purified by means of preparative HPLC (method 13). The free base was obtained from the resulting formate salt of the title compound by percolation of a methanolic solution of the salt through a hydrogencarbonate cartridge (from Polymerlabs, Stratospheres SPE, PL-HCO3 MP SPE, capacity 0.9 mmol). The final purification was effected by extractive stirring in a mixture of 3 ml of pentane and a few drops of diisopropyl ether.

Sources & evidence

ORD record
ord-ad556528ce54479698da0205873fefa2
Source dataset
uspto-grants-2013_06
Patent number
US08470811B2

Reaction notes

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