Potassium Carbonate → benzhydryl (6R,7R)-7-[[(2Z)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 1905107Notes

Reaction equation

HRID 1905107 reaction equation
[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][S:26][C:27]2[S:37][C:30]4=[N:31][C:32]([CH3:36])=[CH:33][C:34](=[O:35])[N:29]4[N:28]=2)[C@H:20]([NH:38][C:39](=[O:68])/[C:40](/[C:43]2[N:44]=[C:45]([NH:48][C:49]([C:62]4[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=4)([C:56]4[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=4)[C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[S:46][CH:47]=2)=[N:41]\[OH:42])[C:19]3=[O:69])=[O:16])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:76][CH2:77][C:78]([O:80][C:81]1[C:89]([O:90][C:91](=[O:94])[CH2:92][Cl:93])=[CH:88][C:84]([C:85](Cl)=[O:86])=[C:83]([CH3:95])[CH:82]=1)=[O:79]>ClCCl>[C:1]1([CH:7]([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][S:26][C:27]2[S:37][C:30]4=[N:31][C:32]([CH3:36])=[CH:33][C:34](=[O:35])[N:29]4[N:28]=2)[C@H:20]([NH:38][C:39](=[O:68])/[C:40](/[C:43]2[N:44]=[C:45]([NH:48][C:49]([C:50]4[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=4)([C:56]4[CH:57]=[CH:58][CH:59]=[CH:60][CH:61]=4)[C:62]4[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=4)[S:46][CH:47]=2)=[N:41]\[O:42][C:85](=[O:86])[C:84]2[CH:88]=[C:89]([O:90][C:91](=[O:94])[CH2:92][Cl:93])[C:81]([O:80][C:78](=[O:79])[CH2:77][Cl:76])=[CH:82][C:83]=2[CH3:95])[C:19]3=[O:69])=[O:16])[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 141247204,5-Bis(chloroacetoxy)-2-methylbenzoyl chlorideHCID 16166547benzhydryl (6R,7R)-7-[[(2Z)-2-hydroxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Product 1

HCID 16166549benzhydryl (6R,7R)-7-[[(2Z)-2-[4,5-bis[(2-chloroacetyl)oxy]-2-methylbenzoyl]oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetyl]amino]-3-[(7-methyl-5-oxo-[1,3,4]thiadiazolo[3,2-a]pyrimidin-2-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of the product obtained in Step 4 (0.6 g) in dry dichloromethane (15 ml) was added potassium carbonate (0.1 g) at once, followed by dropwise addition of a solution of 4,5-bis(chloroacetoxy)-2-methylbenzoyl chloride (0.25 g) in dry dichloromethane (10 ml). The mixture was stirred under ice cooling for one hour and then at room temperature for an additional two hours. After filtering off the insoluble matters, the filtrate was washed with water and with brine, and dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography, giving 0.47 g of the objective compound.

Workup

  1. waitat room temperature for an additional two hours
  2. filtrationAfter filtering off the insoluble matters
  3. washthe filtrate was washed with water and with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe dried solution was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4de67410270542529b4fd64226f182fd
Source dataset
uspto-grants-1989_06
Patent number
US04840945

Reaction notes

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