1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22557098, compound

HRID 394847Notes

Reaction equation

HRID 394847 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=[O:8].[C:9]([O:13][C:14]([NH:16][C:17]([CH3:22])([C:19](O)=[O:20])[CH3:18])=[O:15])([CH3:12])([CH3:11])[CH3:10].CN(C)CCCN=C=NCC>ClCCl>[O:8]=[C:3]1[CH2:4][CH2:5][C:6](=[O:7])[N:2]1[O:1][C:19](=[O:20])[C:17]([NH:16][C:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:15])([CH3:22])[CH3:18]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 80170N-HydroxysuccinimideHCID 2733845N-((1,1-dimethylethoxy)carbonyl)-2-methyl-alanine

Product 1

HCID 22557098HCID 22557098, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of N-hydroxysuccinimide (112 g, 0.973 mol), N-t-butoxycarbonyl-α-methylalanine (197 g, 0.969 mol), and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide (186 g, 0.970 mol) in anhydrous dichloromethane (1.4 L) was stirred at room temperature for about 18 hours under nitrogen atmosphere. The reaction mixture was washed three times each with saturated sodium bicarbonate solution and then brine. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound of Preparation One as a white solid. (256 g, 88%): PBMS (M+18)+318; 1H NMR=250 MHz (CDCl3) δ: 4.91 (NH, br s, 1H), 2.84 (—CO(CH2)2CO—, s, 4H), 1.67 (Me, s, 6H), 1.48 (BOC, s, 9H).

Workup

  1. washThe reaction mixture was washed three times each with saturated sodium bicarbonate solution
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give

Sources & evidence

ORD record
ord-79d0d89228234ce8b463aecbd129214f
Source dataset
uspto-grants-2003_08
Patent number
US06603002B2

Reaction notes

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