Lipoamide → n-Hexyl (2R)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate Ethyl (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate

HRID 351519

Reaction equation

HRID 351519 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2].[CH2:18](O)[CH2:19][CH2:20][CH2:21]CC.C(N(CC)CC)C.C1C(CCCCC(N)=O)SSC1>C(OC(C)(C)C)C>[CH2:1]([O:3][C@H:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH2:9][CH2:18][CH2:19][CH2:20][CH3:21])=[O:6])[CH3:2].[CH2:1]([O:3][C@@H:4]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 863LipoamideHCID 81031-HexanolHCID 8471TriethylamineHCID 11791243Ethyl 2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 86587068n-Hexyl (2R)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate Ethyl (2S)-2-Ethoxy-3-(4-hydroxyphenyl)propanoate

Reagents, catalysts & solvents 1

HCID 12512Ethyl tert-butyl etherSolvent

Procedure

To a solution of ethyl (2RS) (+/−) 2-ethoxy-3-(4-hydroxyphenyl)propanoate in t-butyl ethyl ether (dried on 3 Å molecular sieve) (10 mg/ml) was added n-hexanol (2 equivalents), triethylamine (dried on 3 Å molecular sieve) (14 mol %), 4 Å molecular sieve, and Mucor miehei lipase Lipozyme IM (from Novo Nordisk) (20 mg). The reaction mixture was shaken at room temperature and analysed at different times. The reaction mixture was analysed by the gradient HPLC method 1 and by the chiral CE method 2.

Sources & evidence

ORD record
ord-e6fb5dac0bb84ba68086cd8f7f79a89d
Source dataset
uspto-grants-2004_06
Patent number
US06743608B2

Linked notes

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