Ethanolamine → HCID 22951232, compound

HRID 276689Notes

Reaction equation

[CH3:1][O:2][C:3](=O)[C@H:4]([CH:6]([CH3:8])[CH3:7])[NH2:5].O[CH2:11][C@@H:12](N)[CH:13](C)C.OCCN.C(=O)C(C)C>>[CH:12]([CH:1]1[NH:5][C@@H:4]([CH:6]([CH3:8])[CH3:7])[CH2:3][O:2]1)([CH3:13])[CH3:11]

Participants

Reactant 4

HCID 700Ethanolamine

HCID 6561Isobutyraldehyde

HCID 94285Valine methyl ester

HCID 640993L-Valinol

Product 1

HCID 22951232HCID 22951232, compound

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-fe6148e9fcb74187aba3cb607512ea09
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06353006B1

Reaction notes

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