(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid → (6R)-3-(aminomethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 329932ノート

反応式

HRID 329932 の反応式
[N:1]([CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:28])/[C:18](/[C:22]3[N:23]=[C:24]([NH2:27])[S:25][CH:26]=3)=[N:19]\[O:20][CH3:21])[C:14](=[O:29])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12])=[N+]=[N-]>[Ni].CO.CO.C(O)(C(F)(F)F)=O>[NH2:1][CH2:4][C:5]1[CH2:6][S:7][C@@H:8]2[CH:15]([NH:16][C:17](=[O:28])/[C:18](/[C:22]3[N:23]=[C:24]([NH2:27])[S:25][CH:26]=3)=[N:19]\[O:20][CH3:21])[C:14](=[O:29])[N:9]2[C:10]=1[C:11]([OH:13])=[O:12]

参加物

5

反応物 1

HCID 141548216(6R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(azidomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

生成物 1

HCID 88601874(6R)-3-(aminomethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid収率 45%

試薬・触媒・溶媒 3

HCID 935Nickel触媒HCID 887Methanol溶媒2 回HCID 86669916Methanol trifluoroacetic acid溶媒

実験手順

To a stirred suspension of Raney nickel (16 g.) in MeOH (13 ml.) at 0° was added a solution of 3-azidomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid (2.96 g.) in MeOH/TFA (14 ml., 1.13 ml.). After effervescence ceased the mixture was diluted with MeOH and filtered through paper. The filtrate was evaporated, the residue purified by HPLC using water/HOAc/MeOH 79:1:20 v/v/v as eluant and the product dried over P2O5 to give 3-aminomethyl-7-[2-(2-aminothiazol-4-yl)-2-((Z)-methoxyimino)acetamido]ceph-3-em-4-carboxylic acid trifluorocetate (yield 45%) having the following n.m.r. in solvent A:--3.5-4.2 (m, 4 H); 3.9 (s, 3 H); 5.15 (d, 1 H); 5.85 (d, 1 H); 6.75 (s, 1 H). The corresponding zwitterionic form was produced by passing an aqueous solution through an ion exchange column.

後処理

  1. filtrationfiltered through paper
  2. customThe filtrate was evaporated
  3. customthe residue purified by HPLC
  4. dry with materialthe product dried over P2O5

出典と根拠

ORDレコード
ord-cf87f4decf364e38bebcc013bfe202e3
出典データセット
uspto-grants-1990_01
特許番号
US04894371

反応ノート

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