1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69546047, compound

HRID 2086266Notes

Reaction equation

HRID 2086266 reaction equation
[C:1]([CH2:4][N:5]([S:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:26])[CH:22]=2)[CH:17]=1)(=[O:15])=[O:14])[CH2:6][CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])(O)=[O:2].[C:27]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])(=[O:30])[NH:28][NH2:29].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C(#N)C>[C:32]([O:31][C:27]([NH:28][NH:29][C:1](=[O:2])[CH2:4][N:5]([S:13]([C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[C:21]([Cl:26])[CH:22]=2)[CH:17]=1)(=[O:15])=[O:14])[CH2:6][CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10])=[O:30])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 69545711HCID 69545711, compound

Product 1

HCID 69546047HCID 69546047, compoundYield 102.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of methyl 4-[carboxymethyl(6-chloro-naphthalene-2-sulfonyl)amino]-2-butenate (796 mg), tert-butyl carbazate (265 mg) and HOBt (367 mg) in acetonitrile (20 ml) was combined with WSC (575 mg) and stirred at room temperature for 15 hours. The reaction mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water and brine, dried, concentrated to obtain a residue, which was then crystallized from ether-hexane to obtain methyl 4-[[2-(N′-tert-butoxycarbonylhydrazino)-2-oxoethyl](6-chloro-naphthalene-2-sulfonyl)amino]-2-butenoate (1.05 g) as colorless crystals.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a residue, which
  7. customwas then crystallized from ether-hexane

Sources & evidence

ORD record
ord-ef11b263a8904ad290988d4cca9e2165
Source dataset
uspto-grants-2004_04
Patent number
US06723722B1

Reaction notes

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