1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 69818591, compound

HRID 2417440Notes

Reaction equation

HRID 2417440 reaction equation
[CH2:1]([N:8]([C@H:20]([CH2:40][OH:41])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([C:31]2[CH:39]=[CH:38][C:34]([C:35]([OH:37])=O)=[CH:33][CH:32]=2)=[O:30])=[CH:24][CH:23]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O[N:44]1[C:48]2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.Cl.CN>CN(C)C=O.ClCCCl.C(OCC)(=O)C>[CH2:1]([N:8]([C@H:20]([CH2:40][OH:41])[CH2:21][C:22]1[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:30])[C:31]2[CH:32]=[CH:33][C:34]([C:35]([NH:44][CH3:48])=[O:37])=[CH:38][CH:39]=2)=[CH:26][CH:27]=1)[CH2:9][C@H:10]([OH:19])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6364545Methylamine hydrochlorideHCID 69817718HCID 69817718, compound

Product 1

HCID 69818591HCID 69818591, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[[[4-((2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]phenyl]-amino]carbonyl]benzoic acid (14.6 mg) in N,N-dimethylformamide (200 μl) were added 1.0 M solution of 1-hydroxybenzotriazole hydrate in N,N-dimethylformamide (31.6 μl) and 1.0 M solution of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide in 1,2-dichloroethane (31.6 μl) at room temperature. To the mixture was added methylamine hydrochloride (2.2 mg) and the whole was stirred overnight. The reaction mixture was diluted with ethyl acetate (10 ml) and washed with water (10 ml×1) and brine (10 ml×1) successively, dried over magnesium sulfate, and evaporated to give a pale yellow paste. The crude product was purified by a recycling preparative high pressure liquid chromatography equipped with a gel permeation chromatography column (eluent: chloroform) to give N1-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-3-hydroxypropyl]-phenyl]-N4-methylterephthalamide (14.0 mg) as a white solid.

Workup

  1. washwashed with water (10 ml×1) and brine (10 ml×1) successively
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto give a pale yellow paste
  5. customThe crude product was purified by a recycling preparative high pressure liquid chromatography
  6. customequipped with a gel permeation chromatography column (eluent: chloroform)

Sources & evidence

ORD record
ord-91b1fdc058e54bdda51e7b90653f97c2
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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