HCID 86642586, compound → tert-Butyl methylsulfonylcarbamate

HRID 1873960Notes

Reaction equation

HRID 1873960 reaction equation
COC(C1C2C(=CC(O)=CC=2)N(C2CCCCO2)N=1)C.[C:21]([O:25][C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[C:21]([O:25][C:26]([NH:28][S:29]([CH3:32])(=[O:31])=[O:30])=[O:27])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 86642586HCID 86642586, compoundHCID 135869960HCID 135869960, compound

Product 1

HCID 10081367tert-Butyl methylsulfonylcarbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-(1-Methoxyethyl)-1-(tetrahydro-2H-pyran-2-yl)-indazol-6-ol (30 mg) which can be prepared according to the method described in Reference example 26, etc. and (R)-(3-(2-(N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino)-1-triethylsilyloxy)ethyl)phenyl)-N-tert-butoxycarbonylmethanesulfonamide-toluene solution which can be prepared according to the method described in Reference example 29, etc. [0.34 mL; solution obtained by dissolving (R)-(3-(2-(N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino)-1-triethylsilyloxy)ethyl)phenyl]-N-tert-butoxycarbonylmethanesulfonamide (3.889 g) in toluene (6.60 mL)] were dissolved in toluene (1 mL; manufactured by Kanto Chemical Co., Inc.), added with triphenylphosphine (91.4 mg; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TMAD (66.7 mg; manufactured by Masuda Chemical Industries Co., Ltd.), followed by stirring overnight at room temperature. To the reaction solution, triphenylphosphine (94.5 mg; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TMAD (63.3 mg; manufactured by Masuda Chemical Industries Co., Ltd.) were added and stirred overnight at room temperature. This reaction solution was referred to as “M-1”. Further, 3-(1-methoxyethyl)-1-(tetrahydro-2H-pyran-2-yl)-indazol-6-ol (30 mg) which can be prepared according to the method described in Reference example 26, etc. and (R)-(3-(2-(N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino)-1-triethylsilyloxy)ethyl)phenyl)-N-tert-butoxycarbonylmethanesulfonamide-toluene solution which can be prepared according to the method described in Reference example 29, etc. [0.34 mL; solution obtained by dissolving (R)-(3-(2-(N-tert-butoxycarbonyl-N-(2-hydroxyethyl)amino)-1-triethylsilyloxy)ethyl)phenyl]tert-butoxycarbonylmethanesulfonamide (4.78 g) in dehydrated toluene (8.12 mL)] were dissolved in toluene (1 mL; manufactured by Kanto Chemical Co., Inc.), added with triphenylphosphine (91.4 mg; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TMAD (66.7 mg; manufactured by Masuda Chemical Industries Co., Ltd.) followed by stirring overnight at room temperature. To the reaction solution, triphenylphosphine (94.5 mg; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TMAD (63.3 mg; manufactured by Masuda Chemical Industries Co., Ltd.) were added and stirred overnight at room temperature. This reaction solution was referred to as “M-2”. These “M-1” and “M-2” were purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=85:15→64:34) to obtain the title compound (106.3 mg).

Workup

  1. customcan be prepared

Sources & evidence

ORD record
ord-e658c8f0e2a44f12bc7f5b0f463a39ef
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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