Ammonium Chloride → HCID 3011897, 화합물

HRID 1836270노트

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HRID 1836270 반응식
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

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 67142870HCID 67142870, 화합물HCID 178418339Butyllithium

생성물 1

HCID 3011897HCID 3011897, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-25d3dd77fbb94f6298a757f3f205f7ca
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777395B2

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