Hydrochloric Acid → HCID 15730235, compound

HRID 597154Notes

Reaction equation

HRID 597154 reaction equation
C([NH:3][C@@H:4]1[C:17](=[O:18])[N:6]2[C:7]([C:14]([OH:16])=[O:15])=[C:8]([CH2:11][S:12][CH3:13])[CH2:9][S:10][C@H:5]12)=O.Cl>CO.O>[NH2:3][C@@H:4]1[C:17](=[O:18])[N:6]2[C:7]([C:14]([OH:16])=[O:15])=[C:8]([CH2:11][S:12][CH3:13])[CH2:9][S:10][C@H:5]12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131710686HCID 131710686, compound

Product 1

HCID 15730235HCID 15730235, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(i) 7β-Formamido-3-methylthiomethylceph-3-em-4-carboxylic acid (2.88g) was dissolved in methanol (25 ml.) and the stirred solution was treated with concentrated hydrochloric acid (4.0 ml.). After 1.5 hr. at room temperature the solution was diluted with water (80 ml.) and washed with ethyl acetate (2 × 30 ml.) and ether (2 × 20 ml.), rotary evaporated to remove residual ether, and the pH adjusted to 3.5 with 0.880-ammonia. The precipitate was collected after overnight refrigeration, washed with water (2 × 10 ml), methanol (2 × 10 ml.) and ether (3 × 20 ml.), then dried giving 7β-amino-3-methylthiomethylceph-3-em-4-carboxylic acid as a colourless powder (1.41 g.), m.p. 222°-225° (decomp.), Rf 0.60 (System 2), TLC Rf 0.15, moves 2.0 cm. towards the cathode on electrophoresis at pH 1.9 (3-acetoxymethyl-7β-aminoceph-3-em-4-carboxylic acid moves 1.85 cm. under identical conditions), λmax (pH6 buffer) 266 nm. (ε 9,590), νmax. (Nujol) 1804 (β-lactam), 1536 cm.-1 (carboxylate), τ(D2O with NaHCO3) 4.53 (~0.5-proton doublet, J 4.5 Hz.; C-7 H), 4.88 (1-proton doublet, J 4.5 Hz.; C-6 H), 5.21 (~0.5-proton doublet, J 4.5 Hz.; C-7 H), 6.14, 6.63 [two 1-proton doublets (branches of a quartet), J 18 Hz.; C-2 H2 ], 6.21, 6.68 [two 1-proton doublets (branches of a quartet), J 14 Hz.; C-3 CH2 ], 7.95 (3-proton singlet; SCH3) [Found: C, 41.2; H, 4.6; N, 10.2; S, 23.6. C9H12N2O3S (260) requires C, 41.5; H, 4.6; N, 10.8; S, 24.6%].

Workup

  1. washwashed with ethyl acetate (2 × 30 ml.) and ether (2 × 20 ml.)
  2. customrotary evaporated
  3. customto remove residual ether
  4. customThe precipitate was collected after overnight refrigeration
  5. washwashed with water (2 × 10 ml), methanol (2 × 10 ml.) and ether (3 × 20 ml.)
  6. customdried

Sources & evidence

ORD record
ord-dc62f58d905d4c62b7b55111ba68703a
Source dataset
uspto-grants-1977_03
Patent number
US04013645

Reaction notes

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