N,N-Diethylaniline → HCID 14479242, compound

HRID 1032200Notes

Reaction equation

HRID 1032200 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:11]/[O:12][C@H:13]([C:28]([O:30][CH:31]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])[C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:23])[CH3:22])=[C:16]([O:24][C:25](=[O:27])[CH3:26])[CH:15]=2)/[C:8](O)=[O:9])[N:6]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:55][O:56][C:57]1[CH:78]=[CH:77][C:60]([CH2:61][O:62][C:63]([C:65]2[N:66]3[C@H:69]([S:70][CH2:71][C:72]=2[CH2:73][Cl:74])[C@H:68]([NH2:75])[C:67]3=[O:76])=[O:64])=[CH:59][CH:58]=1.C1(NC2CCCCC2)CCCCC1.CCN(C1C=CC=CC=1)CC.P(Cl)(Cl)(Cl)=O>ClCCl.C(OCC)(=O)C>[CH3:55][O:56][C:57]1[CH:58]=[CH:59][C:60]([CH2:61][O:62][C:63]([C:65]2[N:66]3[C@H:69]([S:70][CH2:71][C:72]=2[CH2:73][Cl:74])[C@H:68]([NH:75][C:8](=[O:9])/[C:7](/[C:5]2[N:6]=[C:2]([NH2:1])[S:3][CH:4]=2)=[N:11]\[O:12][C@H:13]([C:28]([O:30][CH:31]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[O:29])[C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21](=[O:23])[CH3:22])=[C:16]([O:24][C:25](=[O:27])[CH3:26])[CH:15]=2)[C:67]3=[O:76])=[O:64])=[CH:77][CH:78]=1

Participants

8

Reactant 5

HCID 7061N,N-DiethylanilineHCID 7582DicyclohexylamineHCID 24813Phosphorus oxychlorideHCID 14032023HCID 14032023, compoundHCID 14479198HCID 14479198, compound

Product 1

HCID 14479242HCID 14479242, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

To a suspension containing the product obtained in Step 5 (21.8 g) and (6R,7R)-7-amino-3-chloromethyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid p-methoxybenzyl ester p-toluenesulfonate (19.5 g) in dry dichloromethane (250 ml) were added dicyclohexylamine (7.2 ml) and diethylaniline (11.5 ml), and the mixture was cooled to -15° C. A solution of phosphorus oxychloride (3.4 ml) in dry dichloromethane (30 ml) was added dropwise to the suspension over a period of 40 minutes, and the mixture was stirred for 1.5 hours at -15° C. Ethyl acetate (1 liter) was added, and the mixture was washed twice with 1N hydrochloric acid (300 ml), twice with saturated sodium bicarbonate solution (200 ml), then once with brine (300 ml), and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, and the residue was crystallized with ether, giving 29.9 g of the objective compound as pale yellow crystals.

Workup

  1. washthe mixture was washed twice with 1N hydrochloric acid (300 ml), twice with saturated sodium bicarbonate solution (200 ml)
  2. dry with materialonce with brine (300 ml), and dried over anhydrous sodium sulfate
  3. concentrationThe dried solution was concentrated under reduced pressure
  4. customthe residue was crystallized with ether

Sources & evidence

ORD record
ord-66080ce44c734034aef4d979ef6f9634
Source dataset
uspto-grants-1990_09
Patent number
US04956474

Reaction notes

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