1,2-Dichloroethane → 4-[2(S)-Acetylthiomethyl-3-(2-methylphenyl)propionylamino]-2-(S)-hydroxybutyric acid ethyl ester

HRID 1587987Notes

Reaction equation

HRID 1587987 reaction equation
[C:1]([S:4][CH2:5][C@@H:6]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:7]([OH:9])=O)(=[O:3])[CH3:2].C(Cl)CCl.C1C=C[C:25]2N(O)N=[N:28][C:26]=2C=1.CN1CC[O:36]CC1.CCCCCC.[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46]>CN(C=O)C.CO>[CH2:49]([O:48][C:45](=[O:47])[C@@H:46]([OH:36])[CH2:25][CH2:26][NH:28][C:7](=[O:9])[C@@H:6]([CH2:5][S:4][C:1](=[O:3])[CH3:2])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[CH3:50]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 21226206Ethyl acetate hexaneHCID 228417862(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid

Product 1

HCID 572736434-[2(S)-Acetylthiomethyl-3-(2-methylphenyl)propionylamino]-2-(S)-hydroxybutyric acid ethyl ester

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Using a procedure similar to that described in Example 3, combine 2(S)-acetylthiomethyl-3-(2-methylphenyl)propionic acid (1.18 g), the product of Preparation 9 (0.85 g), EDC (1.09 g), HOBT (0.72 g) and N-methylmorpholine (0.52 ml) in DMF (20 ml). Chromatograph the residue on silica gel using hexane:ethyl acetate 3:2 as eluant to obtain the title compound as a white solid, m.p. 48°-52° C., [α]D26 =-25.9° (MeOH).

Sources & evidence

ORD record
ord-779fa37fc2dc40639078c4a6cf38d039
Source dataset
uspto-grants-1993_06
Patent number
US05219886

Reaction notes

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