Cyclohexyl isothiocyanate → N-cyclohexyl-8,8-dioxo-5-oxa-8lambda6-thia-7-azaspiro[3.5]non-6-en-6-amine

HRID 72356

反応式

HRID 72356 の反応式
[OH:1][C:2]1([CH2:6][S:7]([NH2:10])(=[O:9])=[O:8])[CH2:5][CH2:4][CH2:3]1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH:21]1([N:27]=[C:28]=S)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.BrN1C(=O)CCC1=O>CN1C(=O)CCC1.C1COCC1.O>[CH:21]1([NH:27][C:28]2[O:1][C:2]3([CH2:6][S:7](=[O:9])(=[O:8])[N:10]=2)[CH2:5][CH2:4][CH2:3]3)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

参加物

8

反応物 4

HCID 14289Cyclohexyl isothiocyanateHCID 67184N-bromobutanimideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 68288338(1-Hydroxycyclobutyl)methanesulfonamide

生成物 1

HCID 178527134N-cyclohexyl-8,8-dioxo-5-oxa-8lambda6-thia-7-azaspiro[3.5]non-6-en-6-amine

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 13387N-methyl-2-pyrrolidone溶媒2 回

実験手順

Under inert gas, 200 mg of (1-hydroxycyclobutyl)methanesulfonamide were dissolved in 2.5 ml of NMP, and admixed at −10° C. with 0.61 ml of a 2 N solution of sodium bis(trimethylsilyl)amide in THF and, after stirring for 5 minutes, with a solution of 0.19 ml of cyclohexyl isothiocyanate in 0.5 ml of NMP. After stirring at constant temperature for 40 minutes, 215 mg of N-bromosuccinimide were added in 4 portions within 5 minutes, and the reaction solution was stirred for a further 15 minutes. The reaction mixture was diluted with 60 ml of water and extracted twice with 20 ml of ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride solution, dried over MgSO4 and concentrated by rotary evaporation. The residue was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (114.7 mg) was thus obtained with a molecular weight of 272.4 g/mol (C12H20N2O3S); MS (ESI): m/e=273 (M+H+).

後処理

  1. stirringthe reaction solution was stirred for a further 15 minutes
  2. extractionextracted twice with 20 ml of ethyl acetate
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated by rotary evaporation
  6. customThe residue was purified in a purification laboratory by means of preparative HPLC

出典と根拠

ORDレコード
ord-a298771f1d424f8184557e20b29f4ca1
出典データセット
uspto-grants-2014_09
特許番号
US08828994B2

関連ノート

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