1,4-Dioxane → HCID 178484876, compound

HRID 464397Notes

Reaction equation

HRID 464397 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][CH:32]2[CH2:36][CH2:35][NH:34][C:33]2=[O:37])/[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCOCC1.[NH2:44][C@H:45]([C:53]([O:55]C)=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1>CO>[CH3:1][NH:44][C@H:45]([C:53]([OH:55])=[O:54])[CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24](/[C:26](=[N:30]/[O:31][C@H:32]2[CH2:36][CH2:35][NH:34][C:33]2=[O:37])/[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 312751,4-Dioxane3×HCID 736234L-Phenylalanine, methyl esterHCID 13335553(2Z)-2-(2-oxopyrrolidin-3-yl)oxyimino-2-[2-(tritylamino)-1,3-thiazol-4-yl]acetic acid

Product 1

HCID 178484876HCID 178484876, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Conditions

Temperature
50 °C

Procedure

30 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[(2-pyrrolidon-3-yl)oxyimino]acetic acid and 60 ml of methanol are added to 100 ml of dioxane containing 0.5 g of methyl L-phenylalaninate, and the mixture is heated at 50° C. to dissolve said acid therein. 700 ml of dioxane are added to the solution, and the mixture is stirred at room temperature for 5 hours. Crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "Filtrate I"), and 14.3 g of the crude product thus obtained are dissolved in 24 ml of methanol. 280 ml of dioxane are added to the methanol solution. The mixture is stirred at room temperature for 4 hours, and crystalline precipitates are collected by filtration (the filtrate is hereinafter referred to as "Filtrate II"). 12.2 g of (Z)-2-(2-tritylaminothiazol-4-yl)-2-[((3S)-2-pyrrolidon-3-yl)oxyimino]acetic acid methyl L-phenylalaninate salt are obtained.

Workup

  1. dissolutionto dissolve
  2. customCrystalline precipitates
  3. filtrationare collected by filtration (the filtrate
  4. customthus obtained
  5. stirringThe mixture is stirred at room temperature for 4 hours
  6. customcrystalline precipitates
  7. filtrationare collected by filtration (the filtrate

Sources & evidence

ORD record
ord-e73121a1c5124337a6374f6f626d0f7e
Source dataset
uspto-grants-1985_10
Patent number
US04547494

Reaction notes

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