(R)-Solketal → HCID 178436628, compound

HRID 2037331Notes

Reaction equation

HRID 2037331 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]=2[CH3:20])[CH2:4][O:3]1.[CH2:22](C1C=C(C=C(C)C=1O)C#N)C.CC1(C)O[C@H](CO)CO1>>[CH3:1][C:2]1([CH3:21])[O:6][C@H:5]([CH2:7][O:8][C:9]2[C:10]([CH3:20])=[CH:11][C:12]([C:13]([NH:15][OH:16])=[NH:14])=[CH:17][C:18]=2[CH2:19][CH3:22])[CH2:4][O:3]1

Participants

4

Reactant 3

HCID 736056(R)-SolketalHCID 597599503-Ethyl-4-hydroxy-5-methylbenzonitrileHCID 178426655HCID 178426655, compound

Product 1

HCID 178436628HCID 178436628, compound

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 from 3-ethyl-4-hydroxy-5-methyl-benzonitrile and (R)-(2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol; LC-MS**: tR=0.46 min, [M+H]+=309.23; 1H NMR (D6-DMSO): δ1.17 (t, J=7.5 Hz, 3H), 1.33 (s, 3H), 1.38 (s, 3H), 2.25 (s, 3H), 2.57-2.69 (m, 2H), 3.73-3.84 (m, 3H), 4.12 (t, J=7.0 Hz, 1H), 4.39-4.45 (m, 1H), 5.76 (s br, 2H), 7.34 (s, 1H), 7.36 (s, 1H), 9.47 (s, 1H).

Sources & evidence

ORD record
ord-3ba64dd2b97847cd95e825430318102b
Source dataset
uspto-grants-2013_11
Patent number
US08575200B2

Reaction notes

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