Hydrochloric Acid → HCID 131710687, compound

HRID 597155Notes

Reaction equation

HRID 597155 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.[ClH:19]>O1CCOCC1>[ClH:19].[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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131710686HCID 131710686, compound

Product 1

HCID 131710687HCID 131710687, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(ii) A solution of 7β-formamido-3-methylthiomethylceph-3-em-4-carboxylic acid (6.4 g.) in dioxan (50 ml.) was treated with 50% aqueous hydrochloric acid (7 ml.). After 2 hours at room temperature the mixture was freeze-dried. The resulting material was washed with ethyl acetate and ether, and dried to give 7β-amino-3-methylthiomethylceph-3-em-4-carboxylic acid, hydrochloride (5.95 g., 90%) as a white amorphous solid, [α]D + 58.4° (C 1, 3% NaHCO3), λmax. (0.1 M pH 6 phosphate buffer) 265.5 nm. (ε 7,650), νmax. (Nujol) 1782 (β-lactam), 1715 and 1682 (carboxyl) cm-1, τ (D2O - NaHCO3) 6.59 (C-7 H 1-proton doublet, J 4.5 Hz) 6.91 (C-6 H 1-proton doublet, J 4.5 Hz), 6.2 and 6.67 [C-2 H2 two 1-proton doublets (branches of a quartet), J 18 Hz], 6.24 and 6.7 [C-3 CH2 two 1-proton doublets (branches of a quartet), J 13 Hz], and 7.98 (3-proton singlet, CH3S).

Workup

  1. customAfter 2 hours at room temperature the mixture was freeze-dried
  2. washThe resulting material was washed with ethyl acetate and ether
  3. customdried

Sources & evidence

ORD record
ord-e8471a8d5b4845e4954aaaf3be824792
Source dataset
uspto-grants-1977_03
Patent number
US04013645

Reaction notes

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