Formic Acid → HCID 131713474, compound

HRID 1904145Notes

Reaction equation

HRID 1904145 reaction equation
[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:55])[C:22]([C:30]4[N:31]=[C:32]([NH:35]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:33][CH:34]=4)=[N:23][O:24][CH2:25][CH2:26][N:27]=[N+:28]=[N-:29])[C:18](=[O:56])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.C(O)=O>C(=O)(O)[O-].[Na+]>[CH3:1][N:2]1[C:6]([S:7][CH2:8][C:9]2[CH2:10][S:11][C@@H:12]3[CH:19]([NH:20][C:21](=[O:55])[C:22]([C:30]4[N:31]=[C:32]([NH2:35])[S:33][CH:34]=4)=[N:23][O:24][CH2:25][CH2:26][N:27]=[N+:28]=[N-:29])[C:18](=[O:56])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 131713473HCID 131713473, compound

Product 1

HCID 131713474HCID 131713474, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 1.336 g of the product of Step A and 7 ml of formic acid were stirred at 50° C. for 15 minutes and was vacuum filtered to remove triphenylcarbinol. The filtrate was evaporated to dryness and the residue was taken up in water. After efflorescence, the mixture was vacuum filtered to obtain 0.77 g of raw product which was dissolved in minimum of aqueous 10% sodium bicarbonate solution. 0.77 g of activated carbon were added thereto and the mixture was vacuum filtered. Formic acid was added to the filtrate to adjust the pH to 2 and the mixture was vacuum filtered to obtain 0.171 g of syn isomer of 3-[(1-methyl-1H-tetrazol-5-yl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-(2-azidoethoxyimino)-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. filtrationfiltered
  2. customto remove triphenylcarbinol
  3. customThe filtrate was evaporated to dryness
  4. filtrationfiltered
  5. customto obtain 0.77 g of raw product which
  6. addition0.77 g of activated carbon were added
  7. filtrationfiltered
  8. additionFormic acid was added to the filtrate
  9. filtrationfiltered

Sources & evidence

ORD record
ord-bf7750a3c1184fa2969948c536262c40
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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