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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 70027385, compound

HRID 1356452
Notes
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Reaction equation

HRID 1356452 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.[NH2:25][CH2:26][CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32].CCN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1>C1COCC1.C(N(CC)CC)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:25][CH2:26][CH2:27][N:28]([CH3:36])[C:29](=[O:35])[O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:17])=[CH:11][CH:10]=2)=[CH:3][CH:2]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 2756424N-Boc-N-methylethylenediamineHCID 17817500HCID 17817500, compound

Product 1

HCID 70027385HCID 70027385, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
HCID 8471TriethylamineSolvent

Procedure

4-(4-Biphenylylmethoxy)phenylacetic acid (1.51 g), tert-butyl 2-aminoethyl(methyl)carbamate (826 mg), WSC (1 g), 1-hydroxybenzotriazole (798 mg), and triethylamine (2.2 ml) were added to THF (90 ml). The reaction mixture was stirred at room temperature for 20 hr and poured onto water, followed by extraction with ethyl acetate-THF (1:1). The organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride sequentially, dried with sodium sulfate, and concentrated. The residue was purified by alumina column chromatography (eluent; methanol:THF=1:1) followed by recrystallization from THF-IPE gave the titled compound (888 mg).

Workup

  1. additionpoured onto water
  2. extractionfollowed by extraction with ethyl acetate-THF (1:1)
  3. washThe organic layer was washed with water, saturated aqueous sodium bicarbonate, and saturated aqueous sodium chloride sequentially
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by alumina column chromatography (eluent; methanol:THF=1:1)
  7. customfollowed by recrystallization from THF-IPE

Sources & evidence

ORD record
ord-9bfb135552dd4683b5c981d4566ca64e
Source dataset
uspto-grants-2003_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06586475B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes