1-Butanol → 7-(Thien-2-ylacetamido)-3-(2-carbamoylmethyl-1,3,4-oxadiazol-5-ylthio)methylceph-3-em-4-carboxylic acid

HRID 2049559Notes

Reaction equation

HRID 2049559 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[O:33][C:32]([CH2:34][C:35]([NH2:37])=[O:36])=[N:31][N:30]=1.C(=O)(O)[O-].[Na+].C(O)CCC>P([O-])([O-])([O-])=O.C(O)C.O.C(O)(=O)C>[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[O: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

9

Reactant 4

HCID 2631-ButanolHCID 516892Sodium BicarbonateHCID 23675321Cephalothin SodiumHCID 178513877HCID 178513877, compound

Product 1

HCID 705889987-(Thien-2-ylacetamido)-3-(2-carbamoylmethyl-1,3,4-oxadiazol-5-ylthio)methylceph-3-em-4-carboxylic acid

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 1061PhosphateSolvent

Procedure

Sodium cephalothin (2.09 g, 5.0 mmole), 5-mercapto-1,3,4-oxadiazol-2-ylacetamide (0.84 g., 5.5 mmole) and sodium bicarbonate (0.42 g., 5.0 mmole) in pH 6.5 phosphate buffer (25 ml) were heated at 60° C. for 6.5 hours, then poured onto crushed ice (~25 g), washed with ethyl acetate (2×20 ml), acidified to pH 2.0 with N hydrochloric acid and extracted with ethyl acetate (3×50 ml). The extracts were washed with water (2×20 ml) and saturated brine (20 ml), dried and evaporated to dryness in vacuo to give a gummy solid. This was extracted with hot ethyl acetate (10 ml) to leave the product as an off white solid, 1.23 g., 49.8%; t.l.c. (SiO2 ; n-butanol, acetic acid, water; 12:3:5) Rf=0.41; λmax (95% ethanol), 272 nm (εm=9,650); δ[(CD3)2SO], 3.5-4.0 (2H,m, C2 methylene), 3.85 and 3.90 (4H, 2×s, 2×--CH2CO--), 4.33 and 4.49 (2H, AB quartet, J=14 Hz, --CH2S--), 5.22 (1H,d, J=5 Hz, C6 proton), 5.81 (1H,dd, J=5,8 Hz, C7 proton), 7.0-7.6 (3 H,m, thienyl protons), 7.65 (2H, d, J=26 Hz, --CONH2 ), 9.33 (1H,d, J=8 Hz, --CONH--).

Workup

  1. additionpoured
  2. washwashed with ethyl acetate (2×20 ml)
  3. extractionextracted with ethyl acetate (3×50 ml)
  4. washThe extracts were washed with water (2×20 ml) and saturated brine (20 ml)
  5. customdried
  6. customevaporated to dryness in vacuo
  7. customto give a gummy solid
  8. extractionThis was extracted with hot ethyl acetate (10 ml)
  9. customto leave the product as an off white solid, 1.23 g

Sources & evidence

ORD record
ord-8b3ab5538d82480db8d4659b029c44a4
Source dataset
uspto-grants-1980_04
Patent number
US04198406

Reaction notes

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