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

HRID 5161
Notes
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Reaction equation

HRID 5161 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176
Acetic Acid
Solvent
HCID 313Hydrochloric AcidSolvent2×
HCID 8471TriethylamineSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-80f62c1c46ba4eb9a6ba6a91577ca2ab
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05243043

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes