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Sodium Chloride → n-Hexanoyloxymethyl 7-(2-[2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

HRID 1074742
Notes
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Reaction equation

HRID 1074742 reaction equation
P(Cl)(Cl)Cl.[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:38][O:39][CH3:40])[C:12]([NH:14][CH:15]2[C:36](=[O:37])[N:17]3[C:18]([C:24]([O:26][CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])=[C:19]([Cl:23])[CH2:20][S:21](=O)[C@H:16]23)=[O:13])[N:10]=1.[Cl-].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[NH2:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:38][O:39][CH3:40])[C:12]([NH:14][CH:15]2[C:36](=[O:37])[N:17]3[C:18]([C:24]([O:26][CH2:27][O:28][C:29](=[O:35])[CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[O:25])=[C:19]([Cl:23])[CH2:20][S:21][C@H:16]23)=[O:13])[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 131712436n-Hexanoyloxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 131712435n-Hexanoyloxymethyl 7-(2-[2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate
Yield 27.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phosphorus trichloride (210 mg.) was added to a solution of n-hexanoyloxymethyl 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate-1-oxide (syn-isomer: 570 mg.) in dry dimethylformamide (10 ml.) at -30° C., and stirred at -20° to -30° C. for 50 minutes. 10% Aqueous solution (50 ml.) of sodium chloride was added to the resultant solution, adjusted to pH 8.0 with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then concentrated under reduced pressure. The residue (560 mg.) was purified with column chromatography on silica gel (20 g.) (eluent:ethyl acetate), and the resultant residue (180 mg.) was pulverized with n-hexane (10 ml.) and diethyl ether (5 ml.) to give n-hexanoyloxymethyl 7-[2-(2-amino-4-thiazolyl)- 2-methoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn-isomer: 150 mg.).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium bicarbonate
  3. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue (560 mg.) was purified with column chromatography on silica gel (20 g.) (eluent:ethyl acetate)

Sources & evidence

ORD record
ord-08ec9cca6a054ece83cf5d3472e7bf0f
Source dataset
uspto-grants-1983_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04393059

Reaction notes

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