Water → HCID 86649947、化合物

HRID 2037467ノート

反応式

HRID 2037467 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]2[CH2:22][CH2:21][C@@:20]([C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)([CH2:23][CH2:24][OH:25])[O:19][C:18]2=[O:33])[CH3:16])=[CH:11][CH:10]=1.CCN(CC)CC.[CH3:41][S:42](Cl)(=[O:44])=[O:43].O>C(Cl)Cl>[CH3:41][S:42]([O:25][CH2:24][CH2:23][C@@:20]1([C:26]2[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=2)[O:19][C:18](=[O:33])[N:17]([C@H:15]([C:12]2[CH:13]=[CH:14][C:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])=[CH:10][CH:11]=2)[CH3:16])[CH2:22][CH2:21]1)(=[O:44])=[O:43]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 53361128HCID 53361128、化合物

生成物 1

HCID 86649947HCID 86649947、化合物収率 98.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of (S)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one (50 mg, 0.11 mmol) in dry CH2Cl2 (2 mL) was added Et3N (33 mg, 0.33 mmol) at 0˜−5° C. Then a solution of MsCl (12 mg, 0.13 mmol) in dry CH2Cl2 (1 mL) was added dropwise at the same temperature. After addition, the mixture was allowed to warm to rt gradually. When the reaction was over, water (10 mL) was added. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (3×10 mL). The combined organic layers was washed with 10% citric acid, aqueous NaHCO3 and brine respectively, dried over Na2SO4, filtered and concentrated to give 2-((S)-3-((S)-1-(2′,4′-difluorobi-phenyl-4-yl)ethyl)-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-6-yl)ethyl methanesulfonate (58 mg, crude), which was used for the next step without purification.

後処理

  1. additionAfter addition
  2. additionwas added
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with CH2Cl2 (3×10 mL)
  5. washThe combined organic layers was washed with 10% citric acid, aqueous NaHCO3 and brine respectively
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3d75ffad63594ef7938c63e10c9284ce
出典データセット
uspto-grants-2013_11
特許番号
US08575156B2

反応ノート

読み込み中…