Dimethyl Sulfoxide → HCID 57743091, compound

HRID 1896485Notes

Reaction equation

HRID 1896485 reaction equation
CS(C)=O.C(Cl)(C(Cl)=O)=O.[OH:11][CH2:12][CH:13]([CH2:19][N:20]1[CH2:24][CH:23]([CH2:25][CH2:26][CH3:27])[CH2:22][C:21]1=[O:28])[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C(Cl)Cl>[CH:12]([CH:13]([CH2:19][N:20]1[CH2:24][CH:23]([CH2:25][CH2:26][CH3:27])[CH2:22][C:21]1=[O:28])[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[O:11]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 57743085HCID 57743085, compound

Product 1

HCID 57743091HCID 57743091, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-78 °C

Procedure

In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, DMSO (dried on CaH2, 0.83 g, 0.01 mol) in CH2Cl2 (5 ml) is added onto a solution of (COCl)2 (0.72 g, 0.0052 mol) in CH2Cl2 (5 ml) cooled at −78° C. After 0.5 h at −78° C., ethyl 3-hydroxy-2-[(2-oxo-4-propylpyrrolidin-1-yl)methyl]propanoate x279 (0.92 g, 0.0035 mol) in CH2Cl2 (10 ml) is added, stirred for 2.5 h at −60° C., quenched with Et3N (2.75 ml), stirred overnight at 4° C., washed with saturated NH4Cl and extracted 3 times with CH2Cl2. The combined organic phases are dried over MgSO4, filtered, concentrated in vacuo to give the crude x280 (1.2 g) which is used in the next step without any further purification.

Workup

  1. customquenched with Et3N (2.75 ml)
  2. stirringstirred overnight at 4° C.
  3. washwashed with saturated NH4Cl
  4. extractionextracted 3 times with CH2Cl2
  5. dry with materialThe combined organic phases are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude x280 (1.2 g) which
  9. customis used in the next step without any further purification

Sources & evidence

ORD record
ord-b98b73c358854b96b6f8589899633bc8
Source dataset
uspto-grants-2013_08
Patent number
US08518943B2

Reaction notes

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