Hydrochloric Acid → (6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 261149ノート

反応式

HRID 261149 の反応式
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:25])[C:16]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[N:17][O:18][CH3:19])[C:12](=[O:26])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10].P(OC[C@H]1[O:45][C@@H:44]([N:46]2C3N=CN=C(N)C=3N=C2)[C@H](O)[C@@H]1O)(OP(OP(O)(O)=O)(O)=O)(=O)O.P([O-])([O-])(OC(=O)N)=O.S([O-])([O-])(=O)=O.[Mg+2].Cl>[Cl-].[Mn+2].[Cl-]>[C:44]([O:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:25])[C:16]([C:20]3[O:21][CH:22]=[CH:23][CH:24]=3)=[N:17][O:18][CH3:19])[C:12](=[O:26])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10])(=[O:45])[NH2:46]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 59575'-AtpHCID 24083Sulfuric acid magnesium salt (1:1)HCID 3423467Carbamic acid, monoanhydride with phosphoric acid, ion(2-)HCID 54170549(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid

生成物 1

HCID 41375(6R,7R)-3-(carbamoyloxymethyl)-7-[[2-(2-furanyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid収率 34.4%

試薬・触媒・溶媒 1

HCID 10313134Manganese(2+) dichloride触媒

実験手順

(6R,7R)-3-Hydroxymethyl-7-[2-(fur-2-yl)-2-methoxyiminoacetamido]ceph-3-em-4-carboxylic acid (syn isomer) (40 mg), ATP (300 mg), carbamoyl phosphate (150 mg), magnesium sulphate (20 mg) and manganese chloride (20 mg) were added to a portion of the 0-transcarbamoylase solution (50 ml) prepared in Example 8 and the final volume made up to 100 ml at a pH of 6.75. The mixture was incubated at 28° for 3 hours and was then acidified by addition of conc. hydrochloric acid (2.5 ml), left for 10 mins. and extracted with ethyl acetate. The ethyl acetate layer was back extracted with 0.1 M sodium bicarbonate which was then acidified and re-extracted with ethyl acetate. This extract was dried under reduced pressure and the solid triturated with diethyl ether to afford title compound (15.3 mg) as a dry powder, E1 cm1% 405 (273 nm). The n.m.r. spectrum resembled that of an authentic sample of title compound.

後処理

  1. waitleft for 10 mins
  2. extractionand extracted with ethyl acetate
  3. extractionThe ethyl acetate layer was back extracted with 0.1 M sodium bicarbonate which
  4. extractionre-extracted with ethyl acetate
  5. customThis extract was dried under reduced pressure
  6. customthe solid triturated with diethyl ether

出典と根拠

ORDレコード
ord-1e03d4f41f2a430d8536dcdecc3fdc2d
出典データセット
uspto-grants-1979_08
特許番号
US04164447

反応ノート

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