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

HRID 579734Notes

Reaction equation

HRID 579734 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 of N-((1S)-1-ethoxycarbonyl-3phenylpropyl)-N-(2,2,2-trichloroethoxycarbonyl)alanine (Example 7A) is dissolved in CH2Cl2 and added dropwise to a solution of 4-(2,3-dichloro-4-((ethoxycarbonyl)methoxy)benzoyl)methylene proline ethyl ester and triethylamine in 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-2ba06469a5484b4799245b00a0601fe7
Source dataset
uspto-grants-1988_06
Patent number
US04749698

Reaction notes

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