O-Cresol → HCID 70133461, compound

HRID 1437787Notes

Reaction equation

HRID 1437787 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.COC1C=CC(C[O:14][C:15]([C:17]2[N:22]3[C:23](=[O:35])[CH:24]([NH:25]C(=O)CC4C=CC=CC=4)[C@H:21]3[S:20][CH2:19][C:18]=2[CH:36]=[CH:37][CH3:38])=[O:16])=CC=1.C(O)C(O)C.C1(C)C(O)=CC=CC=1>O.N1C=CC=CC=1.C(Cl)Cl>[NH2:25][CH:24]1[C:23](=[O:35])[N:22]2[C:17]([C:15]([OH:16])=[O:14])=[C:18]([CH:36]=[CH:37][CH3:38])[CH2:19][S:20][C@H:21]12

Participants

8

Reactant 4

HCID 335O-CresolHCID 1030Propylene GlycolHCID 24819Phosphorus pentachlorideHCID 131727474HCID 131727474, compound

Product 1

HCID 70133461HCID 70133461, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

22.8 g of phosphorous pentachloride, 150 ml of methylenechloride, and 8.88 ml of pyridine were added to a 20° C. reactor and stirred for 30 minutes. 30 g (62.6 mmol) of the 7-phenylacetamido-3-[propen-1-yl]-3-cephem-4-carboxylic acid p-methoxybenzyl ester prepared in Example 1 was dropwise added thereto, stirred for 2 hours, and cooled to −10° C. The reaction mixture was stirred for 2 hours after addition of 30 ml of 1,2-propanediol and then for 2 hours after addition of 120 ml of cresol. 200 ml of distilled water was dropwise added to the reaction solution and stirred for 1 hour. After phase separation, an aqueous layer was sent to a crystallization bath and an organic layer was extracted with 300 ml of 2N HCl and then the extract was sent to the crystallization bath. 200 ml of a 30% sodium hydroxide solution was dropwise added to the crystallization bath for crystallization and cooled to 0° C. to precipitate a solid. The solid was filtered and dried in vacuum to give 12 g (50 mmol, yield 80%, Z/E=10.1/1) of the titled compound as a beige solid.

Workup

  1. stirringstirred for 2 hours
  2. stirringThe reaction mixture was stirred for 2 hours
  3. stirringstirred for 1 hour
  4. customAfter phase separation
  5. customan aqueous layer was sent to a crystallization bath
  6. extractionan organic layer was extracted with 300 ml of 2N HCl
  7. addition200 ml of a 30% sodium hydroxide solution was dropwise added to the crystallization bath for crystallization
  8. temperaturecooled to 0° C.
  9. customto precipitate a solid
  10. filtrationThe solid was filtered
  11. customdried in vacuum

Sources & evidence

ORD record
ord-4fac5bea44f94d439c48bf92454ee5a9
Source dataset
uspto-grants-2009_11
Patent number
US07622577B2

Reaction notes

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