1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18508367, compound

HRID 1356457Notes

Reaction equation

HRID 1356457 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16](O)=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:46][CH2:47][CH2:48][NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53]>C1COCC1.C1COCC1.C(OCC)(=O)C>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:46][CH2:47][CH2:48][NH:49][C:50](=[O:56])[O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 187201N-BOC-ethylenediamineHCID 17817500HCID 17817500, compound

Product 1

HCID 18508367HCID 18508367, compoundYield 62.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

To a solution of (4-([1,1′-biphenyl]-4-ylmethoxy)phenyl)acetic acid (2.1 g) in THF (100 ml) were added WSC (1.4 g), HOBt (1 g), and t-butyl N-(2-aminoethyl)carbamate (1 g). After stirring overnight, the reaction mixture was diluted in THF-ethyl acetate, washed with 10% aqueous potassium carbonate, dried, and concentrated. The residue was recrystallized from ethanol to obtain the titled compound (1.8 g).

Workup

  1. washwashed with 10% aqueous potassium carbonate
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-dfae232952cc4053b1dd37eeeedf118c
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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