Butyl Acetate → Deacetylcephalothin

HRID 1283718ノート

反応式

HRID 1283718 の反応式
C([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=O)C.[Na+].C(OCCCC)(=O)C.C([O-])(=O)C.[K+]>O>[OH:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:16]([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C:15](=[O:26])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13]

参加物

5

反応物 3

HCID 31272Butyl AcetateHCID 517044Potassium AcetateHCID 23675321Cephalothin Sodium

生成物 1

HCID 93015Deacetylcephalothin収率 84.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A solution of sodium (6R,7R)-3-acetoxymethyl-7-(thien-2-ylacetamido)ceph-3-em-4-carboxylate (4 g) in demineralised water (80 ml) was treated with a suspension of cells obtained by culture of Rhodosporidium toruloides CBS 14, in a similar manner to that described in Example 1. Deacetylation was shown by t.l.c. to be complete after 42 hours, whereupon the reaction mixture was centrifuged to remove solid matter and the resulting solution was vigorously mixed with butyl acetate (200 ml). The pH of the mixture was adjusted to 2.2 - 2.5 by dropwise addition of concentrated phosphoric acid. The aqueous layer was separated and extracted with further butyl acetate (20 ml), a few drops of Gemex detergent being added to break the emulsion which formed. The butyl acetate fractions were combined and a 12.5% w/v solution of potassium acetate in industrial methylated spirit (≈8 ml) was slowly added thereto, until no further precipitation occurred. The precipitate was isolated by suction filtration, washed with a small volume of acetone and dried under vacuum at room temperature to give the title compound (2.87 g). This was shown by t.l.c. on cellulose-coated plates using an ethyl acetate - n-butanol - sodium acetate solvent system, comparing with an authentic sample and assaying densitometrically, to have a purity of about 75%, indicating an overall yield of 65%.

後処理

  1. customobtained by culture of Rhodosporidium toruloides CBS 14, in a similar manner to that
  2. customto remove solid matter
  3. additionthe resulting solution was vigorously mixed with butyl acetate (200 ml)
  4. additionThe pH of the mixture was adjusted to 2.2 - 2.5 by dropwise addition of concentrated phosphoric acid
  5. customThe aqueous layer was separated
  6. extractionextracted with further butyl acetate (20 ml), a few drops of Gemex detergent
  7. additionbeing added
  8. customformed
  9. customuntil no further precipitation
  10. customThe precipitate was isolated by suction filtration
  11. washwashed with a small volume of acetone
  12. customdried under vacuum at room temperature

出典と根拠

ORDレコード
ord-88aa549f96834f6ba16ba49a00843404
出典データセット
uspto-grants-1976_08
特許番号
US03976546

反応ノート

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