1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 18658487, compound

HRID 1769439Notes

Reaction equation

HRID 1769439 reaction equation
[CH2:1]([O:3][P:4]([CH:9]([NH:18][C@H:19]([C:24](O)=[O:25])[CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[C:27]([O:31][C:32](=[O:46])[C@H:33]([CH2:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1)[NH2:34])([CH3:30])([CH3:29])[CH3:28].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[C:27]([O:31][C:32](=[O:46])[C@H:33]([CH2:35][C:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][CH:37]=1)[NH:34][C:24](=[O:25])[C@H:19]([CH2:20][CH:21]([CH3:22])[CH3:23])[NH:18][CH:9]([P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([CH3:30])([CH3:28])[CH3:29]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 11673459HCID 11673459, compoundHCID 53721009HCID 53721009, compound

Product 1

HCID 18658487HCID 18658487, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 61 mg of N-(1-diethoxyphosphoryl-3-phenylpropyl) -leucine and 39 mg of 3-(α-naphthyl) -L-alanine tert-butyl ester in 1.0 ml of dichloromethane was cooled to 0° C. Then 26 mg of 1-hydroxybenzotriazole monohydrate and 34 mg of 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride was added to the solution which was stirred at 0° C. for 1 hour and then at room temperature for 3 hours. The reaction mixture was diluted with 15 ml of dichloromethane, and the diluted solution was washed with 15 ml of a saturated aqueous solution of sodium bicarbonate and then dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure, and the residue was separated and purified by silica gel chromatography (hexane: ethyl acetate=1:1) to yield the title compound as two mixtures each of which are composed of two stereoisomers (42 mg of a/b mixture, 35 mg of c/d/mixture). (iv) N-[N-(3-phenylphosphonopropyl)leucyl]-3-(α-naphthyl)-L-alanine

Workup

  1. waitat room temperature for 3 hours
  2. washthe diluted solution was washed with 15 ml of a saturated aqueous solution of sodium bicarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. customthe residue was separated
  6. custompurified by silica gel chromatography (hexane: ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d07bd82e6bf14982a5134185d91acd2b
Source dataset
uspto-grants-1995_01
Patent number
US05380921

Reaction notes

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