Triethylamine → tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)methyl]-1,4-oxazepane-4-carboxylate

HRID 1022799Notes

Reaction equation

HRID 1022799 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[NH2:13][C:14]1[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C.[NH2:31][CH2:32][CH:33]1[O:39][CH2:38][CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35][CH:34]1[C:47]1[CH:52]=[CH:51][C:50]([Cl:53])=[C:49]([Cl:54])[CH:48]=1>C1(C)C=CC=CC=1.O>[Cl:54][C:49]1[CH:48]=[C:47]([CH:34]2[CH:33]([CH2:32][NH:31][C:2](=[O:4])[NH:13][C:14]3[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=3[C:16]([O:18][CH3:19])=[O:17])[O:39][CH2:38][CH2:37][N:36]([C:40]([O:42][C:43]([CH3:46])([CH3:45])[CH3:44])=[O:41])[CH2:35]2)[CH:52]=[CH:51][C:50]=1[Cl:53]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 8635Methyl AnthranilateHCID 94429TriphosgeneHCID 66975190tert-butyl (6RS,7SR)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate

Product 1

HCID 66976641tert-butyl (6SR,7RS)-6-(3,4-dichlorophenyl)-7-[({[2-(methoxycarbonyl)phenyl]carbamoyl}amino)methyl]-1,4-oxazepane-4-carboxylateYield 107.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Triphosgene (95 mg) was added to a solution of methyl 2-aminobenzoate (120 mg) and triethylamine (0.17 mL) in toluene (5 mL), and the mixture was stirred at 0° C. for 30 min. To the reaction mixture were added tert-butyl (6SR,7RS)-7-(aminomethyl)-6-(3,4-dichlorophenyl)-1,4-oxazepane-4-carboxylate (300 mg) and triethylamine (0.17 mL), and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (190 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7effc5e432d744e380ae162a731604d9
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

Loading…