Dimethylformamide → HCID 11163547, compound

HRID 855949Notes

Reaction equation

HRID 855949 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11](=[O:20])[NH:12][C@@H:13]1[CH2:17][C:16](=[O:18])[NH:15][C:14]1=[O:19])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:21](Br)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CN(C=O)C>C1COCC1>[CH2:3]([O:10][C:11](=[O:20])[NH:12][C@@H:13]1[CH2:17][C:16](=[O:18])[N:15]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14]1=[O:19])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 44459755Benzyl [(3R)-2,5-dioxopyrrolidin-3-yl]carbamate

Product 1

HCID 11163547HCID 11163547, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.2.2 (via two steps; 2nd step): A suspension of 48.4 mg of 60% NaH in 3 ml of THF was treated with 300 mg of (R)-(2,5-dioxo-pyrrolidin-3-yl)-carbamic acid benzyl ester at 0° C. followed by 161.3 μL of benzyl bromide. After 30 min the resulting precipitate was warmed to rt and treated with 3 ml of DMF to give after 15 min a solution which was stirred for 16 h at rt then quenched with 60 ml of H2O and extracted with 40 ml of toluene. The combined organic layers were dried over MgSO4 and concentrated to give 409 mg (74%) of the (R)-(2,5-dioxo-pyrrolidin-3-yl)-carbamic acid benzyl ester as white crystals; m.p. 145.1-145.5° C. Overall yield for the two step process: 78%.

Workup

  1. customto give after 15 min a solution which
  2. customthen quenched with 60 ml of H2O
  3. extractionextracted with 40 ml of toluene
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-bddbd23d2478409189c542bd18376f23
Source dataset
uspto-grants-2007_08
Patent number
US07262307B2

Reaction notes

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