Dicyclohexylcarbodiimide → HCID 69996954, compound

HRID 1359853Notes

Reaction equation

HRID 1359853 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=C[C:20]2N(O)N=[N:23][C:21]=2[CH:22]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1(N)CC1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[C:14](=[O:16])[NH:23][CH:21]1[CH2:22][CH2:20]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 69996954HCID 69996954, compoundYield 369.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (6 g, 26 mmol), HOBt (0.8 g, 6 mmol) and DCC (5.97 g, 29 mmol) in DCM (260 mL) was added cyclopropylamine (2.1 mL, 31 mmol) and DIPEA (6.8 mL, 39 mmol). The mixture was stirred at rt for overnight. The insolubles were filtered off, the filtrate was concentrated and extracted into ethyl acetate. The organic layer was concentrated and dried to give 6 g of (2S,4R)-2-cyclopropylcarbamoyl-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. filtrationThe insolubles were filtered off
  2. concentrationthe filtrate was concentrated
  3. extractionextracted into ethyl acetate
  4. concentrationThe organic layer was concentrated
  5. customdried

Sources & evidence

ORD record
ord-0abead1cf04348cfb62fca49fa9a6e8a
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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