Dicyclohexylcarbodiimide → HCID 91977270, compound

HRID 35813Notes

Reaction equation

HRID 35813 reaction equation
[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([OH:5])=O.ON1C(=O)CCC1=O.C1CCC(N=C=NC2CCCCC2)CC1.[NH2:36][C@H:37]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH:38]([CH3:40])[CH3:39]>CN(C=O)C>[NH:1]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:2][C:3]([NH:36][C@H:37]([C:41]([O:43][CH2:44][C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)=[O:42])[CH:38]([CH3:40])[CH3:39])=[O:5]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 78288N-(tert-butoxycarbonyl)glycineHCID 80170N-HydroxysuccinimideHCID 6950584benzyl (2S)-2-amino-3-methylbutanoate

Product 1

HCID 91977270HCID 91977270, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-20 °C

Procedure

44 g BocGlyOH (0.25 moles) is dissolved in 250 ml DMF, together with 29 g HOSu. After cooling to -20° C. 52 g DCC dissolved in 250 ml DMF is added. After 4 hours stirring at room temperature 95 g ValOBzl, pTos is added together with 35 ml TEA. After stirring overnight at room temperature, DCU is filtered off, DMF removed and the resulting oil taken up in EtAc and washed with sat. NaCl, sat. NaHCO, and 10% citric acid. The EtAc is dried with Na2SO4, removed by vacuum evaporation and the resulting crystalline mass dried in a desiccator. Yield: 59 g (65%).

Workup

  1. additionis added
  2. filtrationDCU is filtered off
  3. customDMF removed
  4. washwashed with sat. NaCl, sat. NaHCO, and 10% citric acid
  5. dry with materialThe EtAc is dried with Na2SO4
  6. customremoved by vacuum evaporation
  7. customthe resulting crystalline mass dried in a desiccator

Sources & evidence

ORD record
ord-e87f09c186f442838b23a97ad9246f78
Source dataset
uspto-grants-1995_05
Patent number
US05411942

Reaction notes

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