HCID 131713457, compound → HCID 131713459, compound

HRID 1904129Notes

Reaction equation

HRID 1904129 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:55])[C:19]([C:30]3[N:31]=[C:32]([NH:35]C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[S:33][CH:34]=3)=[N:20][O:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])[C:15](=[O:56])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(NCC)C>C(O)=O>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:55])[C:19]([C:30]3[N:31]=[C:32]([NH2:35])[S:33][CH:34]=3)=[N:20][O:21][C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:23])[C:15](=[O:56])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 131713457HCID 131713457, compound

Product 1

HCID 131713459HCID 131713459, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 0.27 g of the product of Step A and 2 ml of 50% aqueous formic acid was stirred at 45° C. for 10 minutes and was thn evaporated to dryness. The residue was triturated with ether and 1.55 g of raw product were recovered which was dissolved in 0.5 ml of methanol. 5 ml of ether were added thereto to recover 0.14 g of the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl-2-(phenylcarbonyloxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. customthn evaporated to dryness
  2. customThe residue was triturated with ether and 1.55 g of raw product
  3. customwere recovered which
  4. dissolutionwas dissolved in 0.5 ml of methanol
  5. addition5 ml of ether were added
  6. customto recover 0.14 g of the syn isomer of 3-acetoxymethyl-7-[2-(2-amino-4-thiazolyl-2-(phenylcarbonyloxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid

Sources & evidence

ORD record
ord-ef2d9496c285471897a497c01b9be1f3
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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