Hydrochloric Acid → HCID 178477370, compound

HRID 2398152Notes

Reaction equation

HRID 2398152 reaction equation
Br[CH2:2][C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[SH:37][C:38]1[N:42](C)[N:41]=[N:40][N:39]=1.[CH2:44](N(CC)CC)C.Cl>O1CCCC1.[Cl-].[Na+].O.C(OCC)(=O)C.O>[CH3:44][CH:2]([S:37][C:38]1[NH:42][N:41]=[N:40][N:39]=1)[C:3]1[CH2:4][S:5][C@@H:6]2[C@H:26]([NH:27][C:28](=[O:35])[CH2:29][C:30]3[S:31][CH:32]=[CH:33][CH:34]=3)[C:25](=[O:36])[N:7]2[C:8]=1[C:9]([O:11][CH:12]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 70592080HCID 70592080, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 178477370HCID 178477370, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of diphenylmethyl 3-bromomethyl-7β-(2-thienylacetamido)-ceph-3-em-4-carboxylate (17.505 g.) and 5-mercapto-1-methyltetrazole (3.486 g.) in dry tetrahydrofuran (250 ml) was stirred at 10° and treated, over 5 minutes, with a solution of triethylamine (4.16 ml) in dry tetrahydrofuran (50 ml). The resulting suspension was stirred for a further 45 minutes (during which time the temperature was allowed to rise to ca. 20°) and then added, over 5 minutes, to a stirred mixture of 2N-hydrochloric acid (50 ml), water (700 ml), brine (700 ml.), and ethyl acetate (1.5 l.). The organic phase was separated, washed with 2N-hydrochloric acid, water and brine, treated with some charcoal and filtered through a pad of kieselguhr. The filtrate was dried and evaporated to a foam (20.6 g.). This foam was dissolved in hot methanol (200 ml.), and the solution cooled to give the ester as colourless plates (14.391 g., 77.5%), λmax. (EtOH) 264 nm. (ε 8,700), νmax. (CHBr3) 3420 (NH), 1780 (β-lactam), 1710 (CO2R), and 1680 and 1502 cm.-1 (CONH), τ (CDCl3) values include 3.40 (NH, doublet, J 9 Hz.), (C-7 H, double doublet, J 5 and 9 Hz.), 5.02 (C-6 H, doublet, J 5 Hz.), 6.19 (CH3).

Workup

  1. customto rise to ca. 20°
  2. customThe organic phase was separated
  3. washwashed with 2N-hydrochloric acid, water and brine
  4. additiontreated with some charcoal
  5. filtrationfiltered through a pad of kieselguhr
  6. customThe filtrate was dried
  7. customevaporated to a foam (20.6 g.)
  8. dissolutionThis foam was dissolved in hot methanol (200 ml.)
  9. temperaturethe solution cooled

Sources & evidence

ORD record
ord-e06b80e54f7945cdb2b3bda26312767c
Source dataset
uspto-grants-1977_05
Patent number
US04024134

Reaction notes

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