Methyl Acrylate → (S)-Methyl 3-(4-(cyclopropyl(2,3-dichlorobenzyl)amino)-1-hydroxy-4-oxobutan-2-ylamino)propanoate

HRID 1092800Notes

Reaction equation

HRID 1092800 reaction equation
[NH2:1][C@H:2]([CH2:19][OH:20])[CH2:3][C:4]([N:6]([CH:16]1[CH2:18][CH2:17]1)[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=1[Cl:15])=[O:5].[C:21]([O:25][CH3:26])(=[O:24])[CH:22]=[CH2:23]>CO>[CH:16]1([N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[C:9]=2[Cl:15])[C:4](=[O:5])[CH2:3][C@H:2]([NH:1][CH2:23][CH2:22][C:21]([O:25][CH3:26])=[O:24])[CH2:19][OH:20])[CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 66590104(S)-3-Amino-N-cyclopropyl-N-(2,3-dichlorobenzyl)-4-hydroxybutanamide

Product 1

HCID 66593719(S)-Methyl 3-(4-(cyclopropyl(2,3-dichlorobenzyl)amino)-1-hydroxy-4-oxobutan-2-ylamino)propanoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

Into a 250 mL round bottom was 4B (10.6 g, 33.4 mmol) and methanol (90 mL). Methyl acrylate (3.16 g, 36.8 mmol, 1.1 eq) was added and the reaction was heated to 50° C. overnight. Solvent was removed under vacuum. The residue was used in the next step without further purification. ESI-MS:m/z 403.3 (M+H)+.

Workup

  1. customSolvent was removed under vacuum
  2. customThe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-286efc364fd4444291b05e0644369ab7
Source dataset
uspto-grants-2012_03
Patent number
US08129538B1

Reaction notes

Loading…