(R)-Solketal → (R)-3-Chloro-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-5-methyl-benzamidine

HRID 1958781Notes

Reaction equation

HRID 1958781 reaction equation
[CH3:1][C:2]1([CH3:21])[O:6][CH:5]([CH2:7][O:8][C:9]2[C:18]([CH3:19])=[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(C)C=1O)C#N.CC1(C)O[C@H](CO)CO1>>[Cl:22][C:10]1[CH:11]=[C:12]([CH:17]=[C:18]([CH3:19])[C:9]=1[O:8][CH2:7][C@@H:5]1[CH2:4][O:3][C:2]([CH3:21])([CH3:1])[O:6]1)[C:13]([NH:15][OH:16])=[NH:14]

Participants

4

Reactant 3

HCID 736056(R)-SolketalHCID 190383483-Chloro-4-hydroxy-5-methylbenzonitrileHCID 178426655HCID 178426655, compound

Product 1

HCID 178426667(R)-3-Chloro-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-N-hydroxy-5-methyl-benzamidine

Procedure

The title compound is obtained as a colorless oil (1.39 g) 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-methyl-benzonitrile and L-α,β-isopropylidene glycerol. LC-MS: tR=0.66 min, [M+H]+=314.96.

Sources & evidence

ORD record
ord-7aaba0f690754c1190f302aea1e5a095
Source dataset
uspto-grants-2013_04
Patent number
US08410151B2

Reaction notes

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