1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69997310, compound

HRID 1359803Notes

Reaction equation

HRID 1359803 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14]([OH:16])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN=C=N[CH2:22][CH2:23][CH2:24][N:25](C)C.C1C=CC2N(O)N=NC=2C=1.C1(N)CC1>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[C@H:9]1[C:14](=[O:16])[NH:25][CH:24]1[CH2:22][CH2:23]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69828CyclopropylamineHCID 757711-HydroxybenzotriazoleHCID 14037017(2S,3S)-1-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 69997310HCID 69997310, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (2S,3S)-3-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (6 g), EDAC (6 g, 1.2 eq.), HOBt (4.2 g, 1.2 eq.), TEA (9 mL, 2.5 eq.) and cyclopropylamine (2.2 mL, 1.2 eq.) in DMF (30 mL) was stirred at rt for over the weekend. The insolubles were filtered off, the filtrate was concentrated, redissolved in ethyl acetate, washed with sodium bicarbonate and brine, dried and concentrated to give 5.6 g of (2S,3S)-2-cyclopropylcarbamoyl-3-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. dissolutionredissolved in ethyl acetate
  4. washwashed with sodium bicarbonate and brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c1997ae870bb4fef9a9e8e9f3c88eff0
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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