Thionyl Chloride → (S)-3-isobutyl-4-carbomethoxy-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine HCl salt

HRID 276503Notes

Reaction equation

HRID 276503 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:13])[C@@H:5]([CH2:11]O)[NH:6][CH2:7][CH:8]([CH3:10])[CH3:9].COC(=O)[C@@H](CO)N.O=S(Cl)[Cl:24].[CH3:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[N:36]=[C:37]=[S:38]>>[ClH:24].[CH3:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[N:36]=[C:37]1[N:6]([CH2:7][CH:8]([CH3:10])[CH3:9])[C@@H:5]([C:4]([O:3][CH3:2])=[O:13])[CH2:11][S:38]1

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 90387Methyl D-serinateHCID 1456212-Methyl-4-nitrophenyl isothiocyanateHCID 88093438(R)-N-isobutylserine methyl ester HCl salt

Product 1

HCID 69993936(S)-3-isobutyl-4-carbomethoxy-2-(2-methyl-4-nitrophenylimino)-1,3-thiazolidine HCl salt

Procedure

(R)-N-isobutylserine methyl ester HCl salt was made from (D)-serine methyl ester as described in Method B3a. The ester was reacted with SOCl2, followed by 2-methyl-4-nitrophenyl isothiocyanate according to Method C2a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-4-(methoxycarbonyl)-3-isobutyl-1,3-thiazolidine HCl salt.

Sources & evidence

ORD record
ord-86a6b6ecdb2d44d49f90b7a3ef551eb1
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…