Ammonia → HCID 67717719, compound

HRID 1683820Notes

Reaction equation

HRID 1683820 reaction equation
[ClH:1].[CH2:2]([O:4][C:5]([CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:30]=[CH:31][C:32]=1[C:33]([N:35]([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])=[O:34])[O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[NH:29])OCC)=[CH:21][CH:20]=1)=[O:6])[CH3:3].[OH-].[Na+].[Cl-].[NH4+].N.Cl.[NH2:48]N=CC1C=CC(OCCCCCOC2C=CC(C(=O)N(C(C)C)C(C)C)=C(C=2)OCC(O)=O)=CC=1.Cl>C(O)C>[ClH:1].[NH2:48][N:29]=[CH:25][C:22]1[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11]2[CH:30]=[CH:31][C:32]([C:33](=[O:34])[N:35]([CH:39]([CH3:41])[CH3:40])[CH:36]([CH3:38])[CH3:37])=[C:9]([CH:10]=2)[O:8][CH2:7][C:5]([O:4][CH2:2][CH3:3])=[O:6])=[CH:20][CH:21]=1

Participants

8

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 19040952HCID 19040952, compoundHCID 67634873HCID 67634873, compound

Product 1

HCID 67717719HCID 67717719, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A stirred, 0° C. solution of ethyl 4-[5-[3-ethoxycarbonylmethoxy-4-[N,N-bis(1-methylethyl)aminocarbonyl]phenoxy]pentyloxy]benzenecarboximidoate monohydrochloride (400 mg, 0.68 mmol) in 25 mL of anhydrous ethanol is treated with 1.36 mL of 1.0N aqueous sodium hydroxide. After stirring 1.5 hours, the reaction is concentrated in vacuo. The resulting 5-[5-[4-(ethoxyiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetic acid is then dissolved in 50 mL of anhydrous ethanol in a pressure tube, and treated with ammonium chloride (500 mg, 9.4 mmol). This mixture is treated with anhydrous ammonia for 2 minutes at 0° C. The pressure tube is sealed and heated to 50° C. for 1 hour. Upon cooling and concentrating in vacuo, the resulting material is purified by chromatography on silica gel (15 g) with 20-30% methanol/dichloromethane as the eluent to afford a colorless foam. The resulting 5-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetic acid monohydrochloride is then dissolved in 150 mL of anhydrous ethanol at 0° C. and treated with anhydrous hydrogen chloride gas over 30 minutes. This solution is stirred at room temperature for 20 hours and the resulting solution is concentrated in vacuo. The resulting material is purified by chromatography on silica gel (15 g) with 5-20% methanol/dichloromethane as the eluent to afford ethyl 5-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetate monohydrochloride as colorless foam; CHN calculated for

Workup

  1. concentrationthe reaction is concentrated in vacuo
  2. dissolutionThe resulting 5-[5-[4-(ethoxyiminomethyl)phenoxy]pentyloxy]-2-[N,N-bis(1-methylethyl)carbamoyl]phenoxyacetic acid is then dissolved in 50 mL of anhydrous ethanol in a pressure tube
  3. customThe pressure tube is sealed
  4. temperatureUpon cooling
  5. concentrationconcentrating in vacuo
  6. customthe resulting material is purified by chromatography on silica gel (15 g) with 20-30% methanol/dichloromethane as the eluent
  7. customto afford a colorless foam
  8. stirringThis solution is stirred at room temperature for 20 hours
  9. concentrationthe resulting solution is concentrated in vacuo
  10. customThe resulting material is purified by chromatography on silica gel (15 g) with 5-20% methanol/dichloromethane as the eluent

Sources & evidence

ORD record
ord-64656c1986774fb5a93dfe5dd8bb252b
Source dataset
uspto-grants-1997_06
Patent number
US05639768

Reaction notes

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