L-Phenylalanine → (2R)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-phenylethyl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxamide

HRID 352338Notes

Reaction equation

HRID 352338 reaction equation
[CH3:1][C:2]1[C:3]([CH3:18])=[C:4]2[O:13][C@:12]([C:15]([OH:17])=O)([CH3:14])[CH2:11][CH2:10][C:5]2=[C:6]([CH3:9])[C:7]=1[OH:8].[NH2:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CO[C:33](=O)[C@H:34](CC(C)C)N>>[O:29]1[CH2:34][CH2:33][O:30][CH:28]1[C@@H:20]([NH:19][C:15]([C@@:12]1([CH3:14])[CH2:11][CH2:10][C:5]2[C:4](=[C:3]([CH3:18])[C:2]([CH3:1])=[C:7]([OH:8])[C:6]=2[CH3:9])[O:13]1)=[O:17])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 3

HCID 6140L-PhenylalanineHCID 65105(+)-L-Leucine methyl esterHCID 65413546-Hydroxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid, (+)-

Product 1

HCID 69891480(2R)-N-[(1S)-1-(1,3-dioxolan-2-yl)-2-phenylethyl]-6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxamide

Procedure

The experimental protocol used is the same as that described for Example 14, with (R)-Trolox being used instead of intermediate 12.1 and the methyl ester of L-phenylalanine replacing the L-Leucine methyl ester. Yellow oil. LC-MS: MH+=426.2.

Sources & evidence

ORD record
ord-4bb1a5b7c46747d083d8a1127c92c740
Source dataset
uspto-grants-2004_06
Patent number
US06747024B1

Reaction notes

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