Formic Acid → HCID 131712156, compound

HRID 443550Notes

Reaction equation

HRID 443550 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:50])[C:22]([C:25]4[N:26]=[C:27]([NH:30]C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[S:28][CH:29]=4)=[N:23][OH:24])[C:18](=[O:51])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1.C(O)=O.O>C(Cl)Cl.C(O)C>[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:50])[C:22]([C:25]4[N:26]=[C:27]([NH2:30])[S:28][CH:29]=4)=[N:23][OH:24])[C:18](=[O:51])[N:13]3[C:14]=2[C:15]([OH:17])=[O:16])=[N:5][N:4]=[N:3]1

Participants

5

Reactant 3

HCID 284Formic AcidHCID 962WaterHCID 131712157HCID 131712157, compound

Product 1

HCID 131712156HCID 131712156, compound

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

A mixture of the product of Step B and 4 ml formic acid containing 1/3 volume of water was stirred for 10 minutes and was then evaporated to dryness. The residue was triturated with 10 ml of water and was then vacuum filtered. The solid was washed with water and empasted with ether to remove triphenyl carbinol. The raw product was dissolved in 15 ml of acetone containing 20% water and the mixture was vacuum filtered. The product was triturated with 10 ml of ethanol to obtain 1 g of raw product which was empasted with 5 ml of a 1-1 methylene chloride-ethanol mixture to obtain 0.6 g of the syn isomer of 3-[(1-methyl-5-tetrazolyl)-thiomethyl]-7-[2-(2-amino-4-thiazolyl)-2-hydroxyimino-acetamido]-ceph-3-eme-4-carboxylic acid.

Workup

  1. customwas then evaporated to dryness
  2. customThe residue was triturated with 10 ml of water
  3. filtrationvacuum filtered
  4. washThe solid was washed with water
  5. customto remove triphenyl carbinol
  6. dissolutionThe raw product was dissolved in 15 ml of acetone containing 20% water
  7. filtrationfiltered
  8. customThe product was triturated with 10 ml of ethanol
  9. customto obtain 1 g of raw product which

Sources & evidence

ORD record
ord-bf9095014e9c42efa34c732152db6ebe
Source dataset
uspto-grants-1981_04
Patent number
US04260747

Reaction notes

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