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Dimethylformamide → HCID 11163547, compound

HRID 2306858
Notes
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Reaction equation

HRID 2306858 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

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-a35c1debb1694fdd9c68e012e10a204a
Source dataset
uspto-grants-2004_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06828442B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes