반응 #5257

ord-80f62c1c46ba4eb9a6ba6a91577ca2ab

반응 방정식

FB(F)F
boron trifluoride
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-amino-cephalosporanic acid
OCc1ccccc1
benzyl alcohol
[NH4+].[OH-]
ammonium hydroxide
FB(F)F
boron trifluoride
NC1C(=O)N2C(C(=O)O)=C(OCc3ccccc3)CS[C@H]12
3-benzyloxy-7-amino-ceph-3-eme-4-carboxylic acid

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타were reacted
  2. 2
    기타to obtain 27.1 g of raw product
  3. 3
    기타precipitation
  4. 4
    여과filtered
  5. 5
    세척the product was rinsed with acetic acid, acetone
  6. 6
    기타ether to obtain 4.6 of product
  7. 7
    여과vacuum filtered
  8. 8
    세척The product was rinsed with water, acetone

실험 절차

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.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US05243043uspto-grants-1993_09