Ethyl Acetate → potassium (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate

HRID 329677

反応式

HRID 329677 の反応式
[N:1]([C:4]1[CH2:5][C@@H:6]2[C@@H:16]([C@H:17]([OH:19])[CH3:18])[C:15](=[O:20])[N:7]2[C:8]=1[C:9]([O:11]CC=C)=[O:10])=[N+:2]=[N-:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(C(CCCC)C([O-])=O)C.[K+:50].C(OCC)(=O)C>C(OCC)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.C(Cl)Cl.C(OCC)(=O)C>[N:1]([C:4]1[CH2:5][C@@H:6]2[C@@H:16]([C@H:17]([OH:19])[CH3:18])[C:15](=[O:20])[N:7]2[C:8]=1[C:9]([O-:11])=[O:10])=[N+:2]=[N-:3].[K+:50]

参加物

8

反応物 4

HCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 14329067allyl (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]carbapen-2-em-3-carboxylateHCID 23669619Potassium 2-ethylhexanoate

生成物 1

HCID 131715759potassium (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 3283Diethyl Ether溶媒HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

A solution of allyl (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]carbapen-2-em-3-carboxylate (42 mg, 0.15 mmol) and triphenylphosphine (12 mg, 0.045 mmol) in 1:1 methylene chloride-ethyl acetate (2.7 ml) is treated with 0.5M potassium 2-ethylhexanoate in ethyl acetate (0.3 ml, 0.15 mmol) and tetrakis(triphenylphosphine)palladium (O) (13.8 mg, 0.012 mmol). The mixture is stirred 15 minutes at ambient temperature under a nitrogen atmosphere, diluted with diethyl ether, and centrifuged. The insoluble pellet is washed with ether and dried under vacuum to afford potassium (5R,6S)-2-azido-6-[(R)-1-hydroxyethyl]-carbapen-2-em-3-carboxylate.

後処理

  1. washThe insoluble pellet is washed with ether
  2. customdried under vacuum

出典と根拠

ORDレコード
ord-1c4e9ced6a424a758fae9631ae9fc7db
出典データセット
uspto-grants-1990_01
特許番号
US04892869

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