Dicyclohexylcarbodiimide → HCID 10354388, compound

HRID 424660Notes

Reaction equation

HRID 424660 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:16]1([N:22]=[C:23]=NC2CCCCC2)CCCCC1.ON1C(=O)CCC1=O>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([N:22]([CH3:23])[CH3:16])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 10354388HCID 10354388, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To 1-(tert-butoxycarbonyl)-L-proline (5.0 g) in DCM (50 ml) at 5° C. was added dicyclohexylcarbodiimide (5.22 g) and N-hydroxysuccinimide (2.91 g). The mixture was stirred at this temperature for 16 h. The solid was filtered and the filtrate cooled to 5° C. To this mixture was added triethylamine (9.80 ml) and dimethylamine hydrochloride (2.80 g). The mixture was stirred at room temperature for 2 days. H2O (50 ml) was added and the phases were separated and the organics were washed with saturated sodium carbonate (2×20 ml) and brine (20 ml). This was then dried (MgSO4) and evaporated to dryness to afford the title compound as a white solid. Yield: 6.0 g.

Workup

  1. filtrationThe solid was filtered
  2. additionTo this mixture was added triethylamine (9.80 ml) and dimethylamine hydrochloride (2.80 g)
  3. stirringThe mixture was stirred at room temperature for 2 days
  4. additionH2O (50 ml) was added
  5. customthe phases were separated
  6. washthe organics were washed with saturated sodium carbonate (2×20 ml) and brine (20 ml)
  7. dry with materialThis was then dried (MgSO4)
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-90282e2b45094138ab2efda148c02cf3
Source dataset
uspto-grants-2012_01
Patent number
US08106063B2

Reaction notes

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