Isopropanol → 3-Isopropoxymethyl-7-amino-ceph-3-eme-4-carboxylic acid

HRID 5160

Reaction equation

HRID 5160 reaction equation
[CH3:1][C:2]([O:4][CH2:5][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.[CH:23](O)(C)C>C(N(CC)CC)C>[CH:2]([O:4][CH2:5][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])([CH3:23])[CH3:1]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6356Boron trifluorideHCID 4413287-Aminocephalosporanic acid

Product 1

HCID 1317167893-Isopropoxymethyl-7-amino-ceph-3-eme-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Using the procedure of Step A of Example 8, 27.2 g of 7-amino-cephalosporanic acid, 170 ml of the etherate of boron trifluoride, 134 ml of isopropanol and 125 ml of triethylamine were reacted to obtain 16.25 g of raw product which was purified by two successive treatments with hot hydrochloric acid and ammonium hydroxide to obtain 5.8 g of 3-isopropoxymethyl-7-amino-ceph-3-eme-4-carboxylic acid.

Workup

  1. customwere reacted
  2. customto obtain 16.25 g of raw product which
  3. customwas purified by two successive treatments with hot hydrochloric acid and ammonium hydroxide

Sources & evidence

ORD record
ord-563744f14f8d4c1594cf03c6eaa41a0e
Source dataset
uspto-grants-1993_09
Patent number
US05243043

Linked notes

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