Trifluoroacetic acid → HCID 86734116, compound

HRID 1729672Notes

Reaction equation

HRID 1729672 reaction equation
C(OC([NH:8][CH:9]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:10]([NH:12][C@@H:13]1[C:38](=[O:39])[N:15]2[C@@H:16]([C:22]([O:24]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:23])[C@@:17]([Cl:21])([CH3:20])[CH2:18][S:19][C@H:14]12)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>>[NH2:8][CH:9]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:10]([NH:12][C@@H:13]1[C:38](=[O:39])[N:15]2[C@@H:16]([C:22]([OH:24])=[O:23])[C@@:17]([Cl:21])([CH3:20])[CH2:18][S:19][C@H:14]12)=[O:11]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 68139873HCID 68139873, compound

Product 1

HCID 86734116HCID 86734116, compoundYield 40%

Procedure

A mixture of benzhydryl 7β-(α-tert.-butoxycarbonylamino-α-phenylacetamido)-3β-chloro-3α-methylcepham-4α-carboxylate (150 mg), trifluoroacetic acid (4 ml), and anisole (1 ml) is stirred at room temperature for 30 minutes, then evaporated in vacuo, The residue is treated with ether to remove soluble material. The insoluble material is 7β-(α-aminophenylacetamido)- 3β-chloro-3α-methylcepham-4α-carboxylic acid trifluoroacetate. The material is mixed with water (1.5 ml) and 25% Amberlite LA-1R is methyl isobutyl ketone (1.5 ml), and stirred for 2 hours to give an insoluble material which is collected by filtration. The solid is washed with water, methyl isobutyl ketone, and ethyl acetate, and dried to give 7β-(α-aminophenylacetamido)-3β-chloro-3α-methylcepham-4α-carboxylic acid (35 mg). Yield: 40%. IR: νmaxNujol 5.8, 5.7, 5.7μ.

Workup

  1. customevaporated in vacuo
  2. additionThe residue is treated with ether
  3. customto remove soluble material
  4. additionThe material is mixed with water (1.5 ml) and 25% Amberlite LA-1R
  5. stirringstirred for 2 hours
  6. customto give an insoluble material which
  7. filtrationis collected by filtration
  8. washThe solid is washed with water, methyl isobutyl ketone, and ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-73546d419a0442ba8e5e8d9c08a96377
Source dataset
uspto-grants-1976_11
Patent number
US03989685

Reaction notes

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