1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 67087180, compound

HRID 2095586Notes

Reaction equation

HRID 2095586 reaction equation
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][CH2:9][NH:10][CH:11]([CH2:14][N:15]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:16]([C:18](OC)=[O:19])[CH3:17])[C:12]#[N:13])([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1.O>[CH2:25]([O:24][C:22]([N:15]1[CH2:14][CH:11]([C:12]#[N:13])[N:10]([CH2:9][CH2:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:32])[C:18](=[O:19])[C@@H:16]1[CH3:17])=[O:23])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 168937Lithium hydroxide, monohydrateHCID 67074365HCID 67074365, compound

Product 1

HCID 67087180HCID 67087180, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 1.0 g (2 mmol) of 4-[({[benzyloxycarbonyl-((S)-1-methoxycarbonyl-ethyl)-amino]-methyl}-cyano-methyl)-amino]-butyric acid tert-butyl ester in 2 ml of THF was added 0.1 g (2 mmol) of lithium hydroxide monohydrate in 0.5 ml of water. The reaction was stirred for 16 h after which time it was evaporated to dryness. The residue was redissolved in 2 ml of DMF and 0.5 g (2 mmol) of EDCI and 0.3 g (2 mmol) of HOBT was added and the mixture stirred for 2 h. The reaction was then evaporated, the residue redissolved in EtOAc, washed with water, brine, dried (Na2SO4) and concentrated to give after flash silica gel column (n-heptane/EtOAc 4:6 to 1:1) the title compound in 78% yield as a colorless gum. MS: 416.3 (MH+).

Workup

  1. customwas evaporated to dryness
  2. dissolutionThe residue was redissolved in 2 ml of DMF
  3. stirringthe mixture stirred for 2 h
  4. customThe reaction was then evaporated
  5. dissolutionthe residue redissolved in EtOAc
  6. washwashed with water, brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-c0980c5e63ca4f7e9a99e0a0d47f4f48
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

Loading…