3-(Trimethylsilyl)oxazolidin-2-one → 7-Aminodeacetoxycephalosporanic acid

HRID 1439265ノート

反応式

HRID 1439265 の反応式
C[Si](C)(C)[N:3]1[CH2:7][CH2:6][O:5][C:4]1=[O:8].C1(C)[CH:16]=[CH:15][C:14]([S:17](O)(=O)=O)=CC=1.[CH2:22]([N:24](CC)CC)[CH3:23].C1(C)C=CC(S(O)(=O)=[O:36])=CC=1.CN(C)C1C=CC=CC=1.NC(N)=S>>[CH3:16][C:15]1[CH2:14][S:17][C@@H:23]2[C@H:22]([NH2:24])[C:4](=[O:8])[N:3]2[C:7]=1[C:6]([OH:36])=[O:5]

参加物

5

反応物 4

HCID 1235143-(Trimethylsilyl)oxazolidin-2-oneHCID 161127Benzenesulfonic acid, 4-methyl-, compd. with N,N-diethylethanamine (1:1)HCID 2723790ThioureaHCID 713535204-Methylbenzene-1-sulfonic acid--N,N-dimethylaniline (1/1)

生成物 1

HCID 334987-Aminodeacetoxycephalosporanic acid収率 347.7%

実験手順

To the above solution, there were added 0.28 mole of 3-trimethylsilyl-2-oxazolidinone (TMSO, 38.2 ml) and 0.02 mole of triethylamine p-toluenesulphonate (8.468 g). After stirring for 15 minutes, the mixture was heated under reflux for 120 minutes. Thereafter 0.1 mole of dimethylaniline p-toluene sulphonate (29.3 g) and 0.12 mole of thiourea (9.13 g) were added and heating was maintained for a further 60 minutes. Thereafter the mixture was concentrated at reduced pressure and water (100 ml) was added to the residue. The pH was adjusted to 8.5 in the presence of methylene chloride, the phenyl-pseudothio-hydantoin was filtered out and the water phase was decanted off. After further adjustment To pH 4.2, the mixture was filtered again to give 7-ADCA (14.9 g) with 70% yield. Identified by its IR spectrum, m.p. 232- 42 (d) and [α] D2 = 105.0° (C = 1%, 0.5 N HCL).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 120 minutes
  3. temperatureheating
  4. temperaturewas maintained for a further 60 minutes
  5. concentrationThereafter the mixture was concentrated at reduced pressure and water (100 ml)
  6. additionwas added to the residue
  7. filtrationthe phenyl-pseudothio-hydantoin was filtered out
  8. customthe water phase was decanted off
  9. filtrationAfter further adjustment To pH 4.2, the mixture was filtered again

出典と根拠

ORDレコード
ord-fab4856869f84449bf843e1ee6bcab46
出典データセット
uspto-grants-1977_11
特許番号
US04058660

反応ノート

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