Hydrochloric Acid → HCID 66593341, compound

HRID 602333Notes

Reaction equation

HRID 602333 reaction equation
[ClH:1].[OH:2][C@H:3]1[CH2:7][N:6](C(OC(C)(C)C)=O)[C@@H:5]([C:15](=[O:30])[NH:16][C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][C:24]3=[O:29])=[CH:19][CH:18]=2)[CH2:4]1>O1CCOCC1>[ClH:1].[O:29]=[C:24]1[CH2:25][O:26][CH2:27][CH2:28][N:23]1[C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:15]([C@H:5]2[CH2:4][C@@H:3]([OH:2])[CH2:7][NH:6]2)=[O:30])=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66593297HCID 66593297, compound

Product 1

HCID 66593341HCID 66593341, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

7.2 300 ml of 4N hydrochloric acid in dioxane are added to a solution of 15 g (37 mmol) of tert-butyl (2R,4R)-4-hydroxy-2-[4-(3-oxomorpholin-4-yl)phenylcarbamoyl]pyrrolidine-1-carboxylate in 200 ml of dioxane, and the mixture is stirred at room temperature for 12 hours. The precipitate is subsequently filtered off, washed with 50 ml of dioxane and 50 ml of diethyl ether and dried in a desiccator, giving 12.64 g (100%) of N-[4-(3-oxomorpholin-4-yl)phenyl]-(2R,4R)-4-hydroxypyrrolidine-2-carboxamide hydrochloride as a white powder. ESI 306.

Workup

  1. filtrationThe precipitate is subsequently filtered off
  2. washwashed with 50 ml of dioxane and 50 ml of diethyl ether
  3. customdried in a desiccator

Sources & evidence

ORD record
ord-d6261f0eed9e4c019db5c83da0ec3492
Source dataset
uspto-grants-2011_03
Patent number
US07906516B2

Reaction notes

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