2-Methyl-4-nitrophenyl isocyanate → (4S)-2-(2-methyl-4-nitrophenylimino)-3-isobutyl-4-isopropyl-1,3-oxazolidine

HRID 276690Notes

Reaction equation

HRID 276690 reaction equation
Cl[CH2:2][C@@H:3]([NH:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH:4]([CH3:6])[CH3:5].[CH3:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[N:22]=[C:23]=[O:24]>>[CH3:12][C:13]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=1[N:22]=[C:23]1[N:7]([CH2:8][CH:9]([CH3:11])[CH3:10])[C@@H:3]([CH:4]([CH3:6])[CH3:5])[CH2:2][O:24]1

Participants

3

Reactant 2

HCID 42964562-Methyl-4-nitrophenyl isocyanateHCID 54135432HCID 54135432, compound

Product 1

HCID 57007669(4S)-2-(2-methyl-4-nitrophenylimino)-3-isobutyl-4-isopropyl-1,3-oxazolidine

Procedure

(L)-Valine methyl ester was reduced to (1S)-1-(hydroxymethyl)-2-methylpropylamine according to Method B1b, Step 2. The 2-hydroxyethylamine was reacted with isobutyraldehyde according to Method B4c, Step 1 to afford (4S)-2,4diisopropyl-1,3-oxazolidine. The oxazolidine was reduced according to Method B4c, Step 2 to give (1S)-1-(hydroxymethyl)-N-isobutyl-2-methylpropylamine. The substituted 2-hydroxyethylamine was reacted with SOCl2 according to Method B7b to give (1S)-1-(chloromethyl)-N-isobutyl-2-methylpropylamine. The chloroethylamine was reacted with 2-methyl-4-nitrophenyl isocyanate according to Method C4a to afford (4S)-2-(2-methyl-4-nitrophenylimino)-3-isobutyl-4-isopropyl-1,3-oxazolidine.

Sources & evidence

ORD record
ord-18e6a2e39cc54158b75626a2d3611f13
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…