Triethylamine → HCID 131710401, compound

HRID 372878Notes

Reaction equation

HRID 372878 reaction equation
[OH:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:26])[CH2:16][CH:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[N:23][O:24][CH3:25])[C:12](=[O:27])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10].[Cl:28][CH2:29][CH2:30][N:31]=[C:32]=[O:33].C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:28][CH2:29][CH2:30][NH:31][C:32]([O:1][CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:13]([NH:14][C:15](=[O:26])[CH2:16][CH:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]3=[N:23][O:24][CH3:25])[C:12](=[O:27])[N:7]2[C:8]=1[C:9]([OH:11])=[O:10])=[O:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 516892Sodium BicarbonateHCID 131710402HCID 131710402, compound

Product 1

HCID 131710401HCID 131710401, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-hydroxymethyl-7β-(2-methoxyiminophenylacetamido)ceph-3-em-4-carboxylic acid (syn-isomer) (0.35 g.), 2-chloroethylisocyanate (0.097 g.) and triethylamine (1.79 g.) in dimethylformamide (10 ml.) was stirred at room temperature for two hours. The reaction mixture was poured into saturated sodium bicarbonate solution, and the aqueous phase washed with ethyl acetate, acidified and extracted with ethyl acetate. The combined extracts were dried, concentrated to ca. 5 ml. and added dropwise with stirring to petroleum spirit (250 ml.). The resulting solid was filtered and dried to give the title acid (0.157 g., 35%) λmax. (pH 6 buffer) 258 nm (ε 16,800), νmax. (Nujol) 3250 (NH), 2600 and 1715 (CO2H), 1700 and 1530 (NHCO2R), 1660 and 1540 cm.-1 (CONH), τ (DMSO-d6) values include 0.22 (doublet J 9 Hz; 7β-NH), 2.3 to 2.6 (multiplet; aromatic protons), 6.05 (singlet; OCH3), 6.40 (multiplet; C-2 CH2 and --CH2Cl), 6.65 (multiplet; -NHCH2).

Workup

  1. washthe aqueous phase washed with ethyl acetate
  2. extractionextracted with ethyl acetate
  3. customThe combined extracts were dried
  4. concentrationconcentrated to ca. 5 ml
  5. additionand added dropwise
  6. filtrationThe resulting solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-41b1025b728e4083bf6e8c49a6d455d4
Source dataset
uspto-grants-1978_05
Patent number
US04092477

Reaction notes

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