4-Hydroxy-3-methoxy-5-methylbenzonitrile → (S)-2-Hydroxy-N-(2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2-methoxy-6-methyl-phenoxy]-propyl)-acetamide

HRID 2069409Notes

Reaction equation

HRID 2069409 reaction equation
C([C:3]1[CH:18]=[C:17]([C:19](=[NH:22])[NH:20][OH:21])[CH:16]=[C:15]([CH3:23])[C:4]=1[O:5][CH2:6][C@@H:7]([OH:14])[CH2:8][NH:9][C:10](=[O:13])[CH2:11][OH:12])C.[OH:24][C:25]1C(C)=CC(C#N)=CC=1OC>>[OH:12][CH2:11][C:10]([NH:9][CH2:8][C@H:7]([OH:14])[CH2:6][O:5][C:4]1[C:15]([CH3:23])=[CH:16][C:17]([C:19](=[NH:22])[NH:20][OH:21])=[CH:18][C:3]=1[O:24][CH3:25])=[O:13]

Participants

3

Reactant 2

HCID 190383184-Hydroxy-3-methoxy-5-methylbenzonitrileHCID 178436630HCID 178436630, compound

Product 1

HCID 178492425(S)-2-Hydroxy-N-(2-hydroxy-3-[4-(N-hydroxycarbamimidoyl)-2-methoxy-6-methyl-phenoxy]-propyl)-acetamide

Procedure

The title compound is obtained as a reddish oil (1.3 g) in analogy to N—((S)-3-[2-ethyl-4-(N-hydroxycarbamimidoyl)-6-methyl-phenoxy]-2-hydroxy-propyl)-2-hydroxy-acetamide starting from 4-hydroxy-3-methoxy-5-methyl-benzonitrile; LC-MS: tR=0.49 min, [M+H]+=327.98.

Sources & evidence

ORD record
ord-d4c1d0aab98e4d1ab568314c1328136b
Source dataset
uspto-grants-2012_10
Patent number
US08299086B2

Reaction notes

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