3-((Tert-butyldiphenylsilyl)oxy)azetidine → HCID 54591440, compound

HRID 1260188Notes

Reaction equation

HRID 1260188 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]4([C:26]([F:29])([F:28])[F:27])[CH2:25][CH2:24]4)=[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]4([C:26]([F:29])([F:28])[F:27])[CH2:25][CH2:24]4)=[CH:19][CH:18]=3)[N:13]=2)[CH:9]=1

Participants

3

Reactant 2

HCID 178425313-((Tert-butyldiphenylsilyl)oxy)azetidineHCID 58072162HCID 58072162, compound

Product 1

HCID 54591440HCID 54591440, compound

Procedure

Analogously to the process described in Example 1, 500 mg (0.993 mmol) of the compound from Example 2A and 464 mg (1.49 mmol) of the compound from Example 8A were used to obtain 289 mg (58% of theory) of the title compound. It was possible here to dispense with the second component step of the process (silyl ether cleavage with TBAF), since the protecting group had already been detached in the course of the first component step. The crude product was purified by means of MPLC (silica gel, eluent: 1:1 cyclohexane/ethyl acetate) and subsequent extractive stirring in a mixture of 25 ml of pentane, 1 ml of diisopropyl ether and 125 μl of dichloromethane.

Sources & evidence

ORD record
ord-de19b0eb22394ff18079a184f16e8e6b
Source dataset
uspto-grants-2013_06
Patent number
US08470811B2

Reaction notes

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