1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 10605652, compound

HRID 2396762Notes

Reaction equation

HRID 2396762 reaction equation
[NH2:1][C@@H:2]([C:15]([NH:17][C@@H:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][C:20](=[O:23])[O:21][CH3:22])=[O:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]#[N:14].[N:31]1([C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])[CH2:55][CH2:54][CH2:53][C@H:32]1[C:33]([NH:35][C@@H:36]([C:42]([NH:44][C@H:45]([C:50](O)=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[C:37]([S:40][CH3:41])([CH3:39])[CH3:38])=[O:34].C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(OCC)(=O)C>[N:31]1([C:56]([O:58][C:59]([CH3:60])([CH3:61])[CH3:62])=[O:57])[CH2:55][CH2:54][CH2:53][C@H:32]1[C:33]([NH:35][C@@H:36]([C:42]([NH:44][C@H:45]([C:50]([NH:1][C@@H:2]([C:15]([NH:17][C@@H:18]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:19][C:20](=[O:23])[O:21][CH3:22])=[O:16])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]#[N:14])=[O:51])[CH2:46][CH:47]([CH3:49])[CH3:48])=[O:43])[C:37]([S:40][CH3:41])([CH3:39])[CH3:38])=[O:34]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10597882HCID 10597882, compoundHCID 10814358HCID 10814358, compound

Product 1

HCID 10605652HCID 10605652, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of H-DTrp(2-CN)-DAsp(OMe)-OtBu (26 mg, prepared in Example (9-b)) and Boc-Pro-DPen(Me)-Leu-OH (33 mg, prepared in Example (9-f)) in DMF (3 mL) were added HOBT·H2O (12 mg) and EDCI·HCl (15 mg) under ice-cooling. The mixture was stirred under ice-cooling for 1 h and at room temperature for 1.5 h. The mixture was diluted with ethyl acetate (30 mL), washed with sat. aq. NaHCO3 (15 mL), 10% aq. citric acid (15 mL) and brine (15 mL) successively, dried over MgSO4 and evaporated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development to give the product (42 mg).

Workup

  1. temperaturecooling
  2. washwashed with sat. aq. NaHCO3 (15 mL), 10% aq. citric acid (15 mL) and brine (15 mL) successively
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=30/1 for development

Sources & evidence

ORD record
ord-686d631f4fc740bd9762199abbcb1309
Source dataset
uspto-grants-1996_02
Patent number
US05494897

Reaction notes

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