Phosphorus oxychloride → HCID 131715153, compound

HRID 979390Notes

Reaction equation

HRID 979390 reaction equation
C([NH:3][C@@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])=[C:8](/[CH:11]=[CH:12]/[C:13]#[C:14][CH2:15][CH3:16])[CH2:9][S:10][C@H:5]12)=O.P(Cl)(Cl)([Cl:37])=O>CO.CCOCC>[ClH:37].[NH2:3][C@@H:4]1[C:33](=[O:34])[N:6]2[C:7]([C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])=[C:8](/[CH:11]=[CH:12]/[C:13]#[C:14][CH2:15][CH3:16])[CH2:9][S:10][C@H:5]12

Participants

5

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18607847HCID 18607847, compound

Product 1

HCID 131715153HCID 131715153, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A stirred suspension of the product of Stage (b) (633 mg) in methanol (5 ml) and ether (5 ml) was treated dropwise with phosphorous oxychloride (250 μl) with ice-bath cooling. After 90 mins the ice-bath was removed and stirring continued for 40 mins at room temperature. The solution was concentrated and added to vigorously stirred ether (75 ml). The precipitated solid was collected by filtration, washed thoroughly with ether and dried in vacuo to give the title compound as a solid (442 mg); νmax (Nujol) 2600 (NH3+), 2200 (C≡C), 1783 cm-1 (β-lactam); τ(DMSO-d6) values include 2.93 (CH=CH--C≡C), 3.74 (--CH=CH--C≡C), 4.66, 4.78 (6H,7H), 7.60 (--C≡C--CH2 --).

Workup

  1. temperaturecooling
  2. customAfter 90 mins the ice-bath was removed
  3. concentrationThe solution was concentrated
  4. additionadded to vigorously stirred ether (75 ml)
  5. filtrationThe precipitated solid was collected by filtration
  6. washwashed thoroughly with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-df81489d3ec64b1683e2306a3af161c7
Source dataset
uspto-grants-1987_05
Patent number
US04666899

Reaction notes

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