Cephalothin Sodium → HCID 70590709, compound

HRID 2049561Notes

Reaction equation

HRID 2049561 reaction equation
CC(O[CH2:5][C:6]1[CH2:23][S:22][C@@H:9]2[C@H:10]([NH:13][C:14]([CH2:16][C:17]3[S:21][CH:20]=[CH:19][CH:18]=3)=[O:15])[C:11](=[O:12])[N:8]2[C:7]=1[C:24]([O-:26])=[O:25])=O.[Na+].[SH:28][C:29]1[S:33][C:32]([CH2:34][C:35]([NH2:37])=[O:36])=[N:31][N:30]=1>>[S:21]1[CH:20]=[CH:19][CH:18]=[C:17]1[CH2:16][C:14]([NH:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:24]([OH:26])=[O:25])=[C:6]([CH2:5][S:28][C:29]3[S:33][C:32]([CH2:34][C:35](=[O:36])[NH2:37])=[N:31][N:30]=3)[CH2:23][S:22][C@H:9]12)=[O:15]

Participants

3

Reactant 2

HCID 23675321Cephalothin SodiumHCID 178513878HCID 178513878, compound

Product 1

HCID 70590709HCID 70590709, compound

Procedure

Sodium cephalothin (1.05 g, 2.5 mmole) and 5-mercapto-1,3,4-thiadiazol-2-yl-acetamide (0.48 g, 2.75 mmole) were reacted together as described in example 1b. The reaction mixture was poured onto ice, washed with ethyl acetate, covered with ethyl acetate and acidified. The product precipitated as a pale yellow solid, this was filtered off, washed with water and ethyl acetate and dried, 0.87 g, (68.1%); t.l.c. (SiO2 ; B.A.W.; 12:3:5) Rf=0.41; νmax (95% ethanol) 276 nm (ε=12300); δ[(CD3)2SO] 3.85 (2H,s, C2 methylene), 3.95 (2H,s, --CH2CONH--), 4.19 (2H,s, --CH2CONH2), 4.41 and 4.67 (2H, AB quartet, J 14 Hz, --CH2S--), 5.22 (1H,d, J 5 Hz, C6 proton), 5.90 (1H,dd, J 5 and 8 Hz, C7 proton), 6.8-8.1 (6H,m, --CO2H, --CONH2 and thienyl protons), 8.85 (1H,d, J 8 Hz, --CONH--).

Workup

  1. additionThe reaction mixture was poured onto ice
  2. washwashed with ethyl acetate
  3. customThe product precipitated as a pale yellow solid
  4. filtrationthis was filtered off
  5. washwashed with water and ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-fc63e982e1a947febc54625a73dc828d
Source dataset
uspto-grants-1980_04
Patent number
US04198406

Reaction notes

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