1-Butanol → 2-Ethoxy-3-[4-(2-heptylaminoethoxy)phenyl]propionic acid ethyl ester

HRID 1744458Notes

Reaction equation

HRID 1744458 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:25][CH2:26][CH3:27])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][C:17](=O)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)[CH3:2].C(O)CCC>C1COCC1>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:25][CH2:26][CH3:27])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:9][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 696256202-Ethoxy-3-[4-(2-heptanoylaminoethoxy)phenyl]propionic acid ethyl ester

Product 1

HCID 696257582-Ethoxy-3-[4-(2-heptylaminoethoxy)phenyl]propionic acid ethyl esterYield 71.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound obtained in Step d (46 mg) in THF (2 ml) was added with borane/dimethyl sulfide complex (55 μl, Tokyo Kasei Kogyo). The reaction mixture was stirred at room temperature for 24 hours, added with butanol (2 ml) and stirred for 2 hours. The reaction mixture was concentrated, and the resulting residue was applied on a silica gel column and eluted with chloroform/methanol (100:5, then 100:10) to obtain the title compound (31.7 mg).

Workup

  1. stirringstirred for 2 hours
  2. concentrationThe reaction mixture was concentrated
  3. washeluted with chloroform/methanol (100:5

Sources & evidence

ORD record
ord-9e12421d172b420196d2ae6b46a507a3
Source dataset
uspto-grants-2006_03
Patent number
US07015345B2

Reaction notes

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