Dicyclohexylcarbodiimide → (2S)-N-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-(1,3-dioxoisoindolin-2-yl)propanamide

HRID 57384Notes

Reaction equation

HRID 57384 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[OH:4].[O:12]=[C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:22])[N:14]1[C@@H:23]([CH3:27])[C:24](O)=[O:25].C(=NC1CCCCC1)=NC1CCCCC1>C1COCC1>[Cl:11][C:8]1[CH:9]=[CH:10][C:5]([CH:3]([OH:4])[CH2:2][NH:1][C:24](=[O:25])[C@@H:23]([N:14]2[C:13](=[O:12])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:22])[CH3:27])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 4124342-Amino-1-(4-chlorophenyl)ethan-1-olHCID 720644Pht-Ala-OH

Product 1

HCID 90416129(2S)-N-(2-(4-chlorophenyl)-2-hydroxyethyl)-2-(1,3-dioxoisoindolin-2-yl)propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-amino-1-(4-chlorophenyl)ethanol (1000 mg, 5.83 mmol) and (S)-2-(1,3-dioxoisoindolin-2-yl)propanoic acid (1280 mg, 5.83 mmol) in THF (20 ml) was added N,N′-methanediylidenedicyclohexanamine (1.1 eq, 1322 mg, 6.41 mmol) and allowed to stir at ambient temperature for 12 hours. Concentrate in vacuo, dilute w/EtOAc, filter washing w/EtOAc, wash w/water, brine, concentrate in vacuo. Used crude directly in the next step. 2 g of white solid. HRMS(B) tR=1.04 min; MS m/z 373.1

Workup

  1. concentrationConcentrate in vacuo
  2. additiondilute w/EtOAc
  3. filtrationfilter
  4. washwashing
  5. washwash w/water, brine
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-65b258f779f54485a655be77610a715f
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

Loading…