Triethylamine → HCID 69375869, compound

HRID 852254Notes

Reaction equation

HRID 852254 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[C:13]1([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[NH2:28])(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Cl.[CH3:37][O:38][C:39](=[O:60])[C@@H:40]([NH2:59])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:58])[C:50]2[C:55]([Cl:56])=[CH:54][CH:53]=[CH:52][C:51]=2[Cl:57])=[CH:44][CH:43]=1>ClCCl>[CH3:37][O:38][C:39](=[O:60])[C@@H:40]([NH:59][C:2]([NH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[S:19]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)(=[O:21])=[O:20])=[O:4])[CH2:41][C:42]1[CH:47]=[CH:46][C:45]([NH:48][C:49](=[O:58])[C:50]2[C:51]([Cl:57])=[CH:52][CH:53]=[CH:54][C:55]=2[Cl:56])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 77956Benzenamine, 2-(phenylsulfonyl)-HCID 94429TriphosgeneHCID 23383932methyl (2S)-2-amino-3-{4-[(2,6-dichlorobenzoyl)amino]phenyl}propionate hydrochloride

Product 1

HCID 69375869HCID 69375869, compoundYield 148.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of triphosgene (0.084 g, 0.28 mmol) in dichloromethane (1 ml) at 0° C. was slowly added a solution of 2-benzenesulfonylphenylamine (0.2 g, 0.87 mmol) in dichloromethane (1 ml) and the mixture was stirred at 0° C. for 15 minutes. After that, triethylamine (0.17 g, 1.74 mmol) in dichloromethane (2 ml) was added dropwise at 0° C. and the reaction was allowed to stir at room temperature for 3 h. To this solution a mixture of (S)-2-amino-3-[4-(2,6-dichlorobenzoylamino)phenyl]propionic acid methyl ester hydrochloride (0.35 g, 0.87 mmol) and triethylamine (0.9 g, 0.87 mmol) in dichloromethane (2 ml) was slowly added and the resulting reaction mixture was stirred at room temperature overnight. The volatiles were removed under reduced pressure and the residue was purified by column chromatography (Flash Biotage, dichloromethane:ethyl acetate 3:1) to yield the title compound (0.26 g, 50%) as a white solid.

Workup

  1. stirringto stir at room temperature for 3 h
  2. additionwas slowly added
  3. customthe resulting reaction mixture
  4. stirringwas stirred at room temperature overnight
  5. customThe volatiles were removed under reduced pressure
  6. customthe residue was purified by column chromatography (Flash Biotage, dichloromethane:ethyl acetate 3:1)

Sources & evidence

ORD record
ord-914edf2451e3464282a9727d67a485c7
Source dataset
uspto-grants-2007_08
Patent number
US07253171B2

Reaction notes

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