HCID 53855123, compound → HCID 54467133, compound

HRID 1385746Notes

Reaction equation

HRID 1385746 reaction equation
C([O:5][C:6]([C@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:48])[CH2:14][N:15]([CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:16]([N:18]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[C:27]([O:29]C(C)(C)C)=[O:28])=[O:21])=[O:17])=[O:7])(C)(C)C>Cl.O1CCOCC1>[CH2:41]([N:15]([CH2:14][C:13]([N:9]1[CH2:10][CH2:11][CH2:12][C@@H:8]1[C:6]([OH:7])=[O:5])=[O:48])[C:16]([N:18]([CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@@H:23]1[C:27]([OH:29])=[O:28])=[O:21])=[O:17])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

4

Reactant 1

HCID 53855123HCID 53855123, compound

Product 1

HCID 54467133HCID 54467133, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 220 mg (0.33 mmol) (R)-1-[[1,3-Dibenzyl-3-[2-[(R)-2-tert-butoxycarbonyl-pyrrolidin-1-yl]-2-oxo-ethyl]-ureido]-acetyl]-pyrrolidine-2-carboxylic acid tert-butyl ester in 5 ml 4 N hydrochloric acid solution in dioxane was stirred for 5 h at room temperature. The product was extracted with 1 N sodium hydroxide solution, the basic extract was acidified with 1 N hydrochloric acid solution to pH 4 and the product extracted with ethyl acetate. The organic phase was dried (magnesium sulfate) and evaporated to give 74 mg (41 %) of the title compound as a brown oil.

Workup

  1. extractionThe product was extracted with 1 N sodium hydroxide solution
  2. extractionthe basic extract
  3. extractionthe product extracted with ethyl acetate
  4. dry with materialThe organic phase was dried (magnesium sulfate)
  5. customevaporated

Sources & evidence

ORD record
ord-1f1b68bfcd2447e48cf617337016648c
Source dataset
uspto-grants-2001_07
Patent number
US06262089B1

Reaction notes

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