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Sodium Chloride → 7beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

HRID 1155434
ノート
印刷プレビュー

反応式

HRID 1155434 の反応式
[N+](C1C=CC(C[O:9][C:10]([C@@H:12]2[N:17]3[C:18](=[O:31])[C@@H:19]([NH:20][C:21](=[O:30])[CH2:22][O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:16]3[S:15][CH:14]=[C:13]2[O:32][CH3:33])=[O:11])=CC=1)([O-])=O.[N+](C1C=CC(COC(C2N3C(=O)[C@@H](NC(=O)COC4C=CC=CC=4)[C@H]3SCC=2OC)=O)=CC=1)([O-])=O.[OH-].[K+].[Cl-].[Na+]>O1CCCC1.C(Cl)Cl>[O:23]([CH2:22][C:21]([NH:20][C@@H:19]1[C:18](=[O:31])[N:17]2[C@@H:12]([C:10]([OH:11])=[O:9])[C:13]([O:32][CH3:33])=[CH:14][S:15][C@H:16]12)=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 12784140HCID 12784140、化合物HCID 70559733HCID 70559733、化合物

生成物 1

HCID 128054427beta-Phenoxyacetamido-3-methoxy-ceph-2-em-4alpha-carboxylic acid

試薬・触媒・溶媒 2

HCID 6344
Dichloromethane
溶媒
HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A solution, prepared at 0° C., of 555 mg (1.11 mmols) of a crude mixture consisting of 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid p-nitrobenzyl ester and 7β-phenoxyacetamido-3-methoxy-ceph-3-em-4-carboxylic acid p-nitrobenzyl ester in the ratio of about 3:1, in 33 ml of tetrahydrofurane, is mixed, whilst stirring, with 16 ml of an 0.1 N potassium hydroxide solution which has been precooled to 0° C. The mixture is stirred for a further 5 minutes at 0° C., 100 ml of ice water and 100 ml of precooled methylene chloride are then added and the whole is stirred up briefly. Addition of 1 ml of saturated aqueous sodium chloride solution causes the two phases to separate. The organic phase is separated off, and the aqueous phase is again washed with 20 ml of methylene chloride, then covered with 50 ml of methylene chloride and acidified with 20 ml of 2 N hydrochloric acid. After shaking up, the organic phase is separated off and the hydrochloric acid solution is extracted twice more with 10 ml of methylene chloride at a time. The combined methylene chloride extracts are dried over sodium sulphate and evaporated in vacuo. The residue is recrystallised from methylene chloride/diethyl ether/pentane and gives 7β-phenoxyacetamido-3-methoxy-ceph-2-em-4α-carboxylic acid of melting point 142°-145° C.

後処理

  1. additionis mixed
  2. customhas been precooled to 0° C
  3. stirringthe whole is stirred up briefly
  4. customto separate
  5. customThe organic phase is separated off
  6. washthe aqueous phase is again washed with 20 ml of methylene chloride
  7. stirringAfter shaking up
  8. customthe organic phase is separated off
  9. extractionthe hydrochloric acid solution is extracted twice more with 10 ml of methylene chloride at a time
  10. dry with materialThe combined methylene chloride extracts are dried over sodium sulphate
  11. customevaporated in vacuo
  12. customThe residue is recrystallised from methylene chloride/diethyl ether/pentane

出典と根拠

ORDレコード
ord-aca40cfb69dd495a994475eeb5398def
出典データセット
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04301278

反応ノート

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