Ammonium Chloride → HCID 3011897、化合物

HRID 2212948ノート

反応式

HRID 2212948 の反応式
C([NH:4][C:5]1[C:6]2[C:13](Br)=[CH:12][N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][O:29]C(=O)C)[C@@H:21]([O:22]C(=O)C)[C@@:16]3([CH3:33])[O:17]C(=O)C)[C:7]=2[N:8]=[CH:9][N:10]=1)(=O)C.C([Li])CCC.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:49])(=O)=O)=CC=1.[Cl-].[NH4+]>C1COCC1.ClCCl>[NH2:4][C:5]1[C:6]2[C:13]([F:49])=[CH:12][N:11]([C@@H:15]3[O:27][C@H:26]([CH2:28][OH:29])[C@@H:21]([OH:22])[C@@:16]3([CH3:33])[OH:17])[C:7]=2[N:8]=[CH:9][N:10]=1

参加物

7

反応物 4

HCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 67142870HCID 67142870、化合物HCID 178418339Butyllithium

生成物 1

HCID 3011897HCID 3011897、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a pre-cooled (−78° C.) solution of the compound from Step B (529 mg, 1.00 mmol) in THF is added butyl lithium (2M in hexanes) (0.5 mL, 1.00 mmol). The resulting solution is stirred at −78° C. for 30 min and then quenched with N-fluorobenzensulfonimide (315 mg, 1.00 mmol) in THF. The resulting solution is very slowly allowed to come to ambient temperature and then poured into a stirred mixture of saturated aqueous ammonium chloride and dichloromethane. The organic phase is evaporated in vacuo and treated with ammonium hydroxide at 55° C. in a closed container overnight. The resulting crude mixture is purified on silica gel using dichloromethane/methanol as the eluent. Fractions containing the desired product are pooled and evaporated in vacuo to give the desired product.

後処理

  1. customto come to ambient temperature
  2. customThe organic phase is evaporated in vacuo
  3. additiontreated with ammonium hydroxide at 55° C. in a closed container overnight
  4. customThe resulting crude mixture is purified on silica gel
  5. additionFractions containing the desired product
  6. customevaporated in vacuo

出典と根拠

ORDレコード
ord-5b86e15cd7ba4d5dad6f9bd69b26b205
出典データセット
uspto-grants-2006_09
特許番号
US07105499B2

反応ノート

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