Triethylamine → 1-((2S)-2-(N-((1S)-1-Ethoxycarbonyl-3-phenylpropyl)amino)propionyl)-4-(2,3-dichloro-4-((ethoxycarbonyl)methoxy)benzoyl)methyleneproline ethyl ester

HRID 1253051Notes

Reaction equation

HRID 1253051 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]([N:15](C(OCC(Cl)(Cl)Cl)=O)[C@H:16]([C:18]([OH:20])=O)[CH3:17])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:2].[CH2:29]([O:31][C:32](=[O:56])[C@@H:33]1[CH2:37][C:36](=[CH:38][C:39](=[O:55])[C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:42]([Cl:53])[C:41]=2[Cl:54])[CH2:35][NH:34]1)[CH3:30].C(N(CC)CC)C>C(Cl)Cl>[CH2:29]([O:31][C:32](=[O:56])[C@@H:33]1[CH2:37][C:36](=[CH:38][C:39](=[O:55])[C:40]2[CH:45]=[CH:44][C:43]([O:46][CH2:47][C:48]([O:50][CH2:51][CH3:52])=[O:49])=[C:42]([Cl:53])[C:41]=2[Cl:54])[CH2:35][N:34]1[C:18](=[O:20])[C@@H:16]([NH:15][C@H:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:17])[CH3:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13376527N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)-N-(2,2,2-trichloroethoxycarbonyl)alanineHCID 573200794-(2,3-Dichloro-4-((ethoxycarbonyl)methoxy)benzoyl)methylene proline ethyl ester

Product 1

HCID 677408261-((2S)-2-(N-((1S)-1-Ethoxycarbonyl-3-phenylpropyl)amino)propionyl)-4-(2,3-dichloro-4-((ethoxycarbonyl)methoxy)benzoyl)methyleneproline ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The acid chloride from 6.7 g (14.7 mmol) of N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)-N-(2,2,2-trichloroethoxycarbonyl)alanine (Example 7A) is dissolved in 25 ml CH2Cl2 and added dropwise to a solution of 6.3 g (14.6 mmol) of 4-(2,3-dichloro-4-((ethoxycarbonyl)-methoxy)benzoyl)methylene proline ethyl ester and 1.6 g (15.8 mmol) of triethylamine in 100 ml CH2Cl2. Further reaction and purification as in example 7A gives the desired amide.

Workup

  1. customFurther reaction and purification as in example 7A

Sources & evidence

ORD record
ord-459e193706be4de2b55594c5246ef384
Source dataset
uspto-grants-1988_05
Patent number
US04746676

Reaction notes

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