Diisopropylethylamine → Benzyl (2S)-3-(2-bromophenyl)-2-{[(2R)-2-bromopropanoyl]amino}-propanoate

HRID 1272523Notes

Reaction equation

HRID 1272523 reaction equation
[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C@@H:5]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[NH2:6].C(N(C(C)C)CC)(C)C.[Br:30][C@H:31]([CH3:35])[C:32](Cl)=[O:33]>ClCCl>[Br:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][C@H:5]([NH:6][C:32](=[O:33])[C@H:31]([Br:30])[CH3:35])[C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 6997261(2R)-2-bromopropionyl chlorideHCID 11716996benzyl (S)-2-bromophenylalaninate

Product 1

HCID 10367385Benzyl (2S)-3-(2-bromophenyl)-2-{[(2R)-2-bromopropanoyl]amino}-propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Introduce 25.7 g of benzyl (S)-2-bromophenylalaninate and 150 ml of dichloromethane into a reactor, then bring the temperature of the reaction mixture to 0° C. and add 20 ml of diisopropylethylamine followed by 13.2 g of (2R)-2-bromopropionyl chloride. Subsequently, bring the mixture to ambient temperature. After stirring for 1 hour at that temperature, wash the mixture with water and then with dilute acetic acid solution, and evaporate off the solvents to yield the title compound.

Workup

  1. customto 0° C.
  2. customto ambient temperature
  3. washwash the mixture with water
  4. customwith dilute acetic acid solution, and evaporate off the solvents

Sources & evidence

ORD record
ord-ea10b4f1cb964df7a4e21cd1dcd2feb1
Source dataset
uspto-grants-2007_04
Patent number
US07208607B1

Reaction notes

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