Water → Faropenem

HRID 1012037ノート

反応式

HRID 1012037 の反応式
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[S:6][C:7]([C@H:18]1[CH2:22][CH2:21][CH2:20][O:19]1)=[C:8]2[C:12]([O:14]CC=C)=[O:13])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Na].C(C(CCCC)C([O-])=O)C.O>C(Cl)Cl.CC(C)=O>[CH3:3][C@@H:2]([OH:1])[C@H:4]1[C:10](=[O:11])[N:9]2[C:8]([C:12]([OH:14])=[O:13])=[C:7]([C@@H:18]3[O:19][CH2:20][CH2:21][CH2:22]3)[S:6][C@H:5]12

参加物

7

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 9949208Faropenem Related Compound 4HCID 131729018HCID 131729018、化合物

生成物 1

HCID 65894Faropenem

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
10 °C

実験手順

Allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-7-oxo-3-[(2R)-tetrahydrofuran-2-yl]-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (72 g, 0.221 mol) was dissolved in methylene chloride (950 ml). The solution was cooled to 10° C. and triphenyl phosphine (2.0 g, 0.0076 mol), sodium-2-ethylhexanoate (39.71 g, 0.239 mol) and tetrakis triphenylphosphine palladium (0) (2.0 g) were added together at 10° C. The reaction mixture was stirred for 1-2 hours at 10-15° C. After the completion of reaction, water (50 ml) was added to the reaction mixture. The reaction mixture was stirred for 15 minutes, followed by the addition of acetone (332.5 ml) and the reaction mixture was cooled to 0° C. The solid so separated from the reaction mixture was filtered, washed with acetone and dried under reduced pressure to obtain the title compound.

後処理

  1. additionwas added to the reaction mixture
  2. stirringThe reaction mixture was stirred for 15 minutes
  3. temperaturethe reaction mixture was cooled to 0° C
  4. customThe solid so separated from the reaction mixture
  5. filtrationwas filtered
  6. washwashed with acetone
  7. customdried under reduced pressure

出典と根拠

ORDレコード
ord-e9fe6b02078a40a6bc5d803c2bbc225a
出典データセット
uspto-grants-2011_07
特許番号
US07977475B2

反応ノート

読み込み中…