(R)-Solketal → 3-chloro-4-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-N'-hydroxy-5-methoxybenzenecarboximidamide

HRID 1958783Notes

Reaction equation

HRID 1958783 reaction equation
[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][O:8][C:9]2[C:18](C)=[CH:17][C:12]([C:13]([NH:15][OH:16])=[NH:14])=[CH:11][C:10]=2C)[CH2:4][O:3]1.[Cl:22]C1C=C(C=C(OC)C=1O)C#N.CC1(C)O[C@H]([CH2:40][OH:41])CO1>>[Cl:22][C:18]1[CH:17]=[C:12]([CH:11]=[C:10]([O:41][CH3:40])[C:9]=1[O:8][CH2:7][C@@H:5]1[CH2:4][O:3][C:2]([CH3:1])([CH3:21])[O:6]1)[C:13]([NH:15][OH:16])=[NH:14]

Participants

4

Reactant 3

HCID 736056(R)-SolketalHCID 12207173-Chloro-4-hydroxy-5-methoxybenzonitrileHCID 178426655HCID 178426655, compound

Product 1

HCID 1784924273-chloro-4-[[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methoxy]-N'-hydroxy-5-methoxybenzenecarboximidamide

Procedure

The title compound is prepared in analogy to rac-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-3,5-dimethyl-benzamidine starting from 3-chloro-4-hydroxy-5-methoxy-benzonitrile and L-α,β-isopropylidene glycerol. LC-MS: tR=0.42 min, [M+H]+=331.17; 1H NMR (D6-DMSO): δ 1.30 (s, 3H), 1.34 (s, 3H), 3.86 (s, 3H), 3.87-3.93 (m, 2H), 4.00-4.12 (m, 2H), 4.36 (quint, J=5.8 Hz, 1H), 5.90 (s, 2H), 7.32 (d, J=2.0 Hz, 1H), 7.34 (d, J=2.0 Hz, 1H), 9.71 (s, 1H).

Sources & evidence

ORD record
ord-ef9c8d2020b24e32a00581a8abe50556
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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