Benzyl Alcohol → 3-Benzyloxy-7-amino-ceph-3-eme-4-carboxylic acid

HRID 5161

反応式

HRID 5161 の反応式
CC(OC[C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.B(F)(F)F.[CH2:23]([OH:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[OH-].[NH4+]>Cl.C(N(CC)CC)C.C(O)(=O)C>[CH2:23]([O:30][C:6]1[CH2:15][S:14][C@@H:9]2[CH:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

8

反応物 4

HCID 244Benzyl AlcoholHCID 6356Boron trifluoride2 回HCID 14923Ammonium HydroxideHCID 4413287-Aminocephalosporanic acid

生成物 1

HCID 1317181153-Benzyloxy-7-amino-ceph-3-eme-4-carboxylic acid

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒2 回HCID 8471Triethylamine溶媒2 回

実験手順

Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 128 ml of the etherate of boron trifluoride, 126 ml of benzyl alcohol and 90 ml of triethylamine were reacted to obtain 27.1 g of raw product. 25 g of the said product and 250 ml of acetic acid were added to 25 ml of the etherate of boron trifluoride followed by the addition of 25 ml of triethylamine which caused precipitation. The mixture was vacuum filtered and the product was rinsed with acetic acid, acetone and then ether to obtain 4.6 of product. 4.8 g of the said product were dissolved at 45° C. in 20 ml of 2N hydrochloric acid and 8 ml of concentrated hydrochloric acid and the solution was treated with activated carbon. 6 ml of ammonium hydroxide were added to the mixture which was then vacuum filtered. The product was rinsed with water, acetone and then ether to obtain 2 g of 3-benzyloxy-7-amino-ceph-3-eme-4-carboxylic acid.

後処理

  1. customwere reacted
  2. customto obtain 27.1 g of raw product
  3. customprecipitation
  4. filtrationfiltered
  5. washthe product was rinsed with acetic acid, acetone
  6. customether to obtain 4.6 of product
  7. filtrationvacuum filtered
  8. washThe product was rinsed with water, acetone

出典と根拠

ORDレコード
ord-80f62c1c46ba4eb9a6ba6a91577ca2ab
出典データセット
uspto-grants-1993_09
特許番号
US05243043

関連ノート

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