1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69995760, compound

HRID 1359697Notes

Reaction equation

HRID 1359697 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13]([OH:15])=O)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].CCN=C=N[CH2:24][CH2:25][CH2:26][N:27](C)C.C1C=CC2N(O)N=NC=2C=1.C1(N)CC1.C(=O)(O)[O-].[Na+]>CN(C=O)C.[Cl-].[Na+].O.C(N(CC)CC)C>[CH2:4]([O:3][C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@@H:12]1[C:13](=[O:15])[NH:27][CH:26]1[CH2:24][CH2:25]1)=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 1112081-benzyl hydrogen (R)-pyrrolidine-1,2-dicarboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 69995760HCID 69995760, compoundYield 92.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of (+)-carbobenzyloxy-D-proline (1.5 g, 6 mmol), EDAC (2.3 g, 2 eq.), HOBt (0.8 g, 2 eq.) in DMF (20 mL) was added triethylamine (1.5 mL) and cyclopropylamine (0.8 mL, 2 eq.). After stirring at RT for 18 h, the reaction was basified with sodium bicarbonate, poured to brine, and followed by extraction with dichloromethane. After concentration of the combined extracts, the residue was purified on a silica gel column eluting with 100% EtOAc to give 1.6 g (92%) of (R)-2-cyclopropylcarbamoyl-pyrrolidine-1-carboxylic acid benzyl ester.

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. customAfter concentration of the combined extracts, the residue was purified on a silica gel column
  3. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-763ffc04425e4213bbe1c3d5288b54ec
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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