Chlorotrimethylsilane → HCID 88720763, compound

HRID 1463156Notes

Reaction equation

HRID 1463156 reaction equation
[NH2:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([OH:12])=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12.C[Si](C)(C)Cl.C(N(CC)CC)C.CC(OC[C:32]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)C(COC(C)=O)=[C:38]2[C:33]=1[CH:34]=[CH:35][CH:36]=[CH:37]2)=O.C1C[O:54][CH2:53]C1>O>[CH:53]([NH:1][CH:2]1[C:13](=[O:14])[N:4]2[C:5]([C:10]([O:12][CH:32]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:45]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)=[O:11])=[C:6]([CH3:9])[CH2:7][S:8][C@H:3]12)=[O:54]

Participants

7

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 13475828(6R)-7-amino-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Product 1

HCID 88720763HCID 88720763, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 7-amino-3-methylceph-3-em-4-carboxylic acid (7.76 g., 0.036 mole) in anhydrous THF at 0°, cooled in an ice-bath, was added trimethylchlorosilane (7.8 g., 9.07 ml., 2 equivalents) and triethylamine (7.3 g., 10 ml., 2 equivalents). After 10 minutes the ice-bath was removed and the mixture left at ambient temperature for 2 hours. To the mixture was added two equivalents of acetic formic mixed anhydride and the mixture was allowed to stand at ambient temperature for a further 1.5 hours. Water (5 ml.) was added, the precipitated triethylamine hydrochloride was filtered off and the filtrate evaporated on a rotatory evaporator. THF (50 ml.) was added to the residual oil and the solution was esterified with diphenyldiazomethane. The product was purified by chromatography on silica using CH2Cl2 /ether 1:1 v/v as eluant to give diphenylmethyl 7-formylamino-3-methylceph-3-em-4-carboxylate.

Workup

  1. temperaturecooled in an ice-bath
  2. customAfter 10 minutes the ice-bath was removed
  3. waitto stand at ambient temperature for a further 1.5 hours
  4. filtrationthe precipitated triethylamine hydrochloride was filtered off
  5. customthe filtrate evaporated on a rotatory evaporator
  6. additionTHF (50 ml.) was added to the residual oil
  7. customThe product was purified by chromatography on silica

Sources & evidence

ORD record
ord-338abc36e7e5410eba4ae44652eeecc6
Source dataset
uspto-grants-1984_07
Patent number
US04463173

Reaction notes

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