Water → HCID 131727234, compound

HRID 556300Notes

Reaction equation

HRID 556300 reaction equation
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][NH:8][C@H:9]([C:14]([OH:16])=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=[O:6])[CH3:3].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.O>CO.CN(C)C=O.CCCCCC>[CH3:3][C:2]([CH3:17])([O:4][C:5]([NH:7][NH:8][C@H:9]([C:14]([O:16][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:15])[CH2:10][C:11](=[O:13])[NH2:12])=[O:6])[CH3:1]

Participants

8

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 57428061HCID 57428061, compound

Product 1

HCID 131727234HCID 131727234, compoundYield 51%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8058HexaneSolvent

Procedure

The compound was prepared according to Bioorg. Med. Chem., 6 (1998) 1185-1208. N-[(1,1-dimethylethoxycarbonyl)amino]-L-asparagine (20.7 g, 89.1 mmol, 1 eq.), of Step 1, was dissolved in methanol (500 ml) and cesium carbonate (15.97 g, 49 mmol, 0.55 eq.) was added. The solvent was evaporated to give a white solid that was dissolved in N,N-dimethylformamide (200 ml). To the suspension, benzyl bromide (11.6 ml, 98 mmol, 1.1 eq.) was added dropwise and the mixture was stirred overnight. The solvent was reduced under reduced pressure, water (300 ml) was added and the mixture extracted with ethyl acetate (200 ml), washed with brine (50 ml) and the solvent removed under reduced pressure to give a crude that was suspended in n-hexane (160 ml), filtered and dried under vacuum to give 14.68 g of white solid. Yield 51%.

Workup

  1. customThe compound was prepared
  2. customThe solvent was evaporated
  3. customto give a white solid
  4. additionwas added
  5. extractionthe mixture extracted with ethyl acetate (200 ml)
  6. washwashed with brine (50 ml)
  7. customthe solvent removed under reduced pressure
  8. customto give a crude that
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-cb209f9f69ff46d19100ce8d4e7a4db9
Source dataset
uspto-grants-2011_11
Patent number
US08058262B2

Reaction notes

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