tert-Butyl carbonate → HCID 123603902, compound

HRID 713701Notes

Reaction equation

HRID 713701 reaction equation
[C:1](=[O:8])([O-])[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[Si:9]([O:16][C@H:17]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C@@H:18]1[NH:22][CH:21]([CH2:23][C:24]2[CH:25]=[CH:26][C:27]([NH2:30])=[N:28][CH:29]=2)[CH2:20][CH2:19]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]>>[NH2:30][C:27]1[N:28]=[CH:29][C:24]([CH2:23][C@@H:21]2[CH2:20][CH2:19][C@H:18]([C@H:17]([O:16][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[N:22]2[C:1]([O:2][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:8])=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 4613278tert-Butyl carbonateHCID 131734055HCID 131734055, compound2×

Product 1

HCID 123603902HCID 123603902, compoundYield 27%

Procedure

To a solution of 121 mg (0.30 mmol) of 5-({(5R)-5-[(R)-([tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidin-2-yl}methyl)pyridin-2-amine in 5 mL of anhydrous THF (from Step B above) was added tert-butyl carbonate (66 mg, 0.30 mmol), followed by TEA (42 μL, 0.30 mmol) and the resulting solution stirred at room temperature under nitrogen atmosphere overnight. The reaction mixture was put directly on a preparative plate (1500 μM) and eluted with 60% ethyl acetate in hexane to afford the title compound (40.3 mg, 27%). LC-MS: C28H43N3O3Si calculated 497.23 found m/z (ES) 498.2 (MH)+ and 398.2 (M-Boc)+.

Workup

  1. washeluted with 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-11a1b6deef894bd09390167caef10956
Source dataset
uspto-grants-2015_11
Patent number
US09186354B2

Reaction notes

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