Water → HCID 68646332、化合物

HRID 2402776ノート

反応式

HRID 2402776 の反応式
[OH:1][CH2:2][C@:3]([NH:15]C(=O)OC(C)(C)C)([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)[CH3:4].[Cl:23]S([N:27]=[C:28]=[O:29])(=O)=O.O.C(=O)([O-])O.[Na+]>C(#N)C>[ClH:23].[C:28](=[O:29])([O:1][CH2:2][C@:3]([NH2:15])([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:12])([F:13])[F:14])[CH:6]=1)[CH3:4])[NH2:27]

参加物

6

反応物 4

HCID 962WaterHCID 70918Chlorosulfonyl isocyanateHCID 516892Sodium BicarbonateHCID 59536722HCID 59536722、化合物

生成物 1

HCID 68646332HCID 68646332、化合物収率 90.4%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

A solution of 520 mg (1.63 mmol) of the compound from Example 70A in 10 ml of acetonitrile was cooled to −15° C. and admixed with 198 μl (2.28 mmol) of chlorosulphonyl isocyanate. After 10 min, 18 ml of water were added and the mixture was heated at 60° C. overnight. After cooling to RT, the solution was rendered alkaline by addition of saturated aqueous sodium hydrogen carbonate solution and extracted three times with ethyl acetate. The combined organic phases were dried over sodium sulphate and freed from the solvents on a rotary evaporator. For complete deprotection of the amino group, the residue was admixed with 5 ml of a 4M solution of hydrogen chloride in dioxane, and this mixture was stirred at RT for 5 min and concentrated on a rotary evaporator. Drying of the residue in an HV gave the title compound (440 mg, 90% of theory).

後処理

  1. temperatureAfter cooling to RT
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over sodium sulphate
  4. customfreed from the solvents on a rotary evaporator
  5. concentrationconcentrated on a rotary evaporator
  6. customDrying of the residue in an HV

出典と根拠

ORDレコード
ord-96a0cc710cb6499f9e111c053dae2a9f
出典データセット
uspto-grants-2014_08
特許番号
US08796324B2

反応ノート

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