Dicyclohexylcarbodiimide → HCID 15602370, compound

HRID 35812

Reaction equation

HRID 35812 reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][C:4](=[O:6])[NH2:5].ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:40][CH2:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43]>CN(C=O)C>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:40][CH2:41][C:42]([O:44][CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)=[O:43])=[O:9])[CH2:3][C:4](=[O:6])[NH2:5]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 82035N2-((tert-Butoxy)carbonyl)-L-asparagineHCID 409140Benzyl glycinate

Product 1

HCID 15602370HCID 15602370, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

58 g BocAsnOH (0.25 moles) and 29 g HOSu are dissolved in 250 ml DMF and cooled to -20°. 52 g DCC dissolved in 250 ml DMF is added. After 4 hours stirring at room temperature 85 g GlyOBzl, pTos and 35 ml TEA is added. After stirring overnight the DCU i filtered off, DMF removed in vacuo on a Rotavap, and the resulting oil dissolved in EtAc. After extraction with sat. NaCl, sat. NaHCO3, and 10% citric acid, the solvent is dried with Na2SO4 and evaporated. The resulting crystalline ma is dried in a desiccator. Yield: 64 g (67%).

Workup

  1. temperaturecooled to -20°
  2. additionis added
  3. additionis added
  4. filtrationi filtered off
  5. customDMF removed in vacuo on a Rotavap
  6. dissolutionthe resulting oil dissolved in EtAc
  7. extractionAfter extraction with sat. NaCl, sat. NaHCO3, and 10% citric acid
  8. dry with materialthe solvent is dried with Na2SO4
  9. customevaporated
  10. customThe resulting crystalline ma is dried in a desiccator

Sources & evidence

ORD record
ord-031dd53497104afebe992320752ede0e
Source dataset
uspto-grants-1995_05
Patent number
US05411942

Linked notes

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