Methyl chloroformate → 4-[5-[4-[amino(methoxycarbonylimino)methyl]phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

HRID 2399939Notes

Reaction equation

HRID 2399939 reaction equation
Cl.N[N:3]=[CH:4][C:5]1[CH:34]=[CH:33][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=2[O:31][CH3:32])=[CH:7][CH:6]=1.C([N:37](CC)CC)C.Cl[C:43]([O:45][CH3:46])=[O:44]>C(Cl)Cl>[NH2:3][C:4](=[N:37][C:43]([O:45][CH3:46])=[O:44])[C:5]1[CH:34]=[CH:33][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:30]=[CH:29][C:19]([C:20]([N:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[O:21])=[CH:18][C:17]=2[O:31][CH3:32])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 677447554-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide monohydrochloride

Product 1

HCID 538992724-[5-[4-[amino(methoxycarbonylimino)methyl]phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred, 0° C. solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide monohydrochloride (200 mg) in 4.0 mL anhydrous methylene chloride is treated sequentially with triethylamine (0.068 mL, 0.48 mmol) and methyl chloroformate (39 mg). The solution is stirred 30 minutes, concentrated in vacuo and the resulting solids are partitioned between ethyl acetate and water. The organic layer is washed with water and brine, dried over sodium sulfate and concentrated. The resulting material is purified by chromatography on silica gel (15 g) with 70-100% ethyl acetate/hexanes as the eluent to afford 4-[5-{4-[amino(methoxycarbonylimino)methyl]phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide ##STR16## (i-Prop =isopropyl) as a colorless foam:

Workup

  1. concentrationconcentrated in vacuo
  2. customthe resulting solids are partitioned between ethyl acetate and water
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting material is purified by chromatography on silica gel (15 g) with 70-100% ethyl acetate/hexanes as the eluent

Sources & evidence

ORD record
ord-fa025bb5fdde4c54b31c26c0c6318ae9
Source dataset
uspto-grants-1995_09
Patent number
US05451700

Reaction notes

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