Pyridine → HCID 70611773, compound

HRID 1701673Notes

Reaction equation

HRID 1701673 reaction equation
O(CC([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:37])[CH2:34][O:35][CH3:36])[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:13]1=[O:38])=O)C1C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:46].C(O)C(C)C>C(Cl)Cl.CCOCC>[ClH:46].[NH2:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:37])[CH2:34][O:35][CH3:36])[C:17]([O:19][CH:20]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:18])[C:13]1=[O:38]

Participants

7

Reactant 4

HCID 1049PyridineHCID 6560IsobutanolHCID 24819Phosphorus pentachlorideHCID 53866326HCID 53866326, compound

Product 1

HCID 70611773HCID 70611773, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 600 mg (1.1 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-4-methoxy-2-butenoate and 0.106 ml pyridine in 10 ml of methylene chloride at 0° was added 252 mg (1.32 mmol) of phosphorous pentachloride. The reaction mixture was stirred for 2 hours while it was allowed to warm to 10°. The solution was then cooled to 0° and 0.2 ml of isobutanol was added. After 1 hour at 0°, 150 ml of ether was slowly added. The supernatant liquid was then decanted from the resulting oily residue, which was itself then thoroughly triturated with ether: nmr (CDCl3) δ 2.08 (s, 3, CH3), 3.12 (s, 3, --OCH3), 4.22 (s, 2, --CH2OCH3), 3.92 (m, 2, C4 --H), 4.82 (m, 1, C3 --H), and 7.2 (b, ArH).

Workup

  1. temperatureto warm to 10°
  2. temperatureThe solution was then cooled to 0°
  3. waitAfter 1 hour at 0°
  4. customThe supernatant liquid was then decanted from the resulting oily residue, which
  5. customthen thoroughly triturated with ether

Sources & evidence

ORD record
ord-2276efcb7fce4a1a90b8086dcb0d9293
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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