1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69143965, compound

HRID 914766Notes

Reaction equation

HRID 914766 reaction equation
[C:1]([NH:8][C@@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:37][N:38]1[CH2:43][CH2:42][CH:41]([N:44]2[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]2)[CH2:40][CH2:39]1>ClCCl>[C:1]([NH:8][C@@H:9]([C:13]([N:47]1[CH2:46][CH2:45][N:44]([CH:41]2[CH2:42][CH2:43][N:38]([CH3:37])[CH2:39][CH2:40]2)[CH2:49][CH2:48]1)=[O:15])[CH:10]([CH3:11])[CH3:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 5663241-(1-Methyl-4-piperidinyl)piperazineHCID 637605(2R)-2-(((tert-butoxy)carbonyl)amino)-3-methylbutanoic acid

Product 1

HCID 69143965HCID 69143965, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of Boc-D-valine (5.0 g, 23 mmol) in dichloromethane (230 mL) is added HOBt (3.42 g, 25.3 mmol), followed by EDCI (4.85 g, 25.3 mmol), followed by 4-(1-methylpiperidin-4-yl)piperazine (4.2 g, 23 mmol). After stirring overnight, the solution is washed with saturated aqueous NaHCO3, followed by brine, and then concentrated in vacuo. The residue is chromatographed over silica gel, eluting with a gradient of 0-10% (2 N ammonia/methanol) in chloroform. The product-containing fractions are combined and concentrated in vacuo to give the title product (8.98 g, quantitative) as an off-white solid.

Workup

  1. washthe solution is washed with saturated aqueous NaHCO3
  2. concentrationconcentrated in vacuo
  3. customThe residue is chromatographed over silica gel
  4. washeluting with a gradient of 0-10% (2 N ammonia/methanol) in chloroform
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f61f1515b44e40b1b74ff381d1e8ad49
Source dataset
uspto-grants-2007_09
Patent number
US07265121B2

Reaction notes

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