Triethylamine → HCID 131710050, compound

HRID 1578888Notes

Reaction equation

HRID 1578888 reaction equation
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[C:6]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:7][S:8][C@H:3]12.[S:26]1[CH:30]=[CH:29][CH:28]=[C:27]1[CH2:31][C:32](Cl)=[O:33].C(N(CC)CC)C>C(Cl)Cl>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:6]2[CH2:7][S:8][C@@H:3]3[CH:2]([NH:1][C:32](=[O:33])[CH2:31][C:27]4[S:26][CH:30]=[CH:29][CH:28]=4)[C:24](=[O:25])[N:4]3[C:5]=2[C:17]([O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[O:18])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1623622-Thiopheneacetyl chlorideHCID 131710049HCID 131710049, compound

Product 1

HCID 131710050HCID 131710050, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The free base (XI) (80 mg) was treated with 2-thienylacetyl chloride (40 mg) and triethylamine (0.05 ml) in dry methylene chloride (5 ml) at -20°. After 15 minutes the solution was washed with brine, dried and evaporated. Chromatography on silica gave the cephem (X) (50 mg) which crystallised on trituration with dry ether. νmax (CHCl3) 3380, 1780, 1710, 1685 cm-1

Workup

  1. washAfter 15 minutes the solution was washed with brine
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-1dbc3cdffd60418ab0f355ed754a656e
Source dataset
uspto-grants-1976_02
Patent number
US03939157

Reaction notes

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