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Morpholine → (5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

HRID 1090552
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HRID 1090552 반응식
C(OC([N:7]1[CH2:11][CH:10]([F:12])[CH2:9][C@H:8]1[CH:13]=[C:14]([C:16]1[CH2:22][C@H:21]2[N:18]([C:19](=[O:26])[C@@H:20]2[C@H:23]([OH:25])[CH3:24])[C:17]=1[C:27]([O:29]CC=C)=[O:28])[CH3:15])=O)C=C.N1CCOCC1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C(O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:12][CH:10]1[CH2:11][NH:7][C@H:8]([CH:13]=[C:14]([C:16]2[CH2:22][C@H:21]3[N:18]([C:19](=[O:26])[C@@H:20]3[C@H:23]([OH:25])[CH3:24])[C:17]=2[C:27]([OH:29])=[O:28])[CH3:15])[CH2:9]1
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참가 물질

7

반응물 3

HCID 8083MorpholineHCID 11776TriphenylphosphineHCID 86743911allyl (5R,6S)-3-[2-{(2S)-1-allyloxycarbonyl-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

생성물 1

HCID 57167763(5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid수율 20.2%

시약·촉매·용매

3
HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of allyl (5R,6S)-3-[2-{(2S)-1-allyloxycarbonyl-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.7 g), morpholine (694 μl), and triphenylphosphine (199 mg) in tetrahydrofuran (30 ml) and ethanol (10 ml) was added tetrakis(triphenylphosphine)palladium(0) (263 mg) at room temperature. After stirring for an hour, the precipitate was filtered, washed in turn with dichloromethane (3 times) and acetone (twice), and dried under reduced pressure to give (5R,6S)-3-[2-{(2S)-4-fluoropyrrolidin-2-yl}-1-methylethenyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (248 mg).

후처리

  1. filtrationthe precipitate was filtered
  2. washwashed in turn with dichloromethane (3 times) and acetone (twice), and
  3. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-ec6882b228a34a4d8e7b781cd6aecb93
출처 데이터셋
uspto-grants-1992_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05081237

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