Water → Faropenem

HRID 1012037노트

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HRID 1012037 반응식
[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

참가 물질

7

반응물 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 9949208Faropenem Related Compound 4HCID 131729018HCID 131729018, 화합물

생성물 1

HCID 65894Faropenem

시약·촉매·용매 2

HCID 180Acetone용매HCID 6344Dichloromethane용매

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온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9fe6b02078a40a6bc5d803c2bbc225a
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977475B2

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