Diisopropyl Ether → HCID 14668279, compound

HRID 2255515Notes

Reaction equation

[CH2:1]([C:4]1[C:5]([O:17][CH3:18])=[C:6]([C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=1)[C:7]([OH:9])=O)[CH2:2][CH3:3].S(Cl)(Cl)=O.[CH2:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30][NH2:31])[CH3:24].O(C(C)C)C(C)C>>[CH2:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30][NH:31][C:7](=[O:9])[C:6]1[C:10]([O:15][CH3:16])=[C:11]([O:13][CH3:14])[CH:12]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]=1[O:17][CH3:18])[CH3:24]

Participants

Reactant 4

HCID 7914Diisopropyl Ether

HCID 24386Thionyl Chloride

HCID 643457(S)-(-)-2-Aminomethyl-1-ethylpyrrolidine

HCID 14668268HCID 14668268, compound

Product 1

HCID 14668279HCID 14668279, compound

Procedure

3-Propyl-2,5,6-trimethoxybenzoic acid (23 g, 0.09 mol) was treated with thionyl chloride and (2S)-(-)-1-ethyl-2-aminomethylpyrrolidine as described in example 4. Yield 10.6 g (32%). M.p. 68°-70° C. (i-Pr2O). 1H-NMR (CDCl3): δ6.73 (s,1H), 6.40 (b,1H), 3.85 (Sx2,6H), 3.76 (s,3H), 0.9-3.8 (m,21H)ppm.

Sources & evidence

ORD record: ord-26b8dbcc716a44918e937560b2cb10fc
Source dataset: uspto-grants-1993_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05240957

Reaction notes

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