Lithium Hydroxide → 6-{2-(2-Carboxy-ethyl)-3-[6-(4-oxo-8-propyl-chroman-7-yloxy)-hexyl]-phenoxy}-hexanoic acid
Reaction equation
C[O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([O:20]C)=[O:19])=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]1[CH:39]=[CH:38][C:32]2[C:33](=[O:37])[CH2:34][CH2:35][O:36][C:31]=2[C:30]=1[CH2:40][CH2:41][CH2:42]C1C=CC=CC=1.[OH-].[Li+]>O1CCCC1>[C:18]([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:39]=[CH:38][C:32]3[C:33](=[O:37])[CH2:34][CH2:35][O:36][C:31]=3[C:30]=2[CH2:40][CH2:41][CH3:42])[C:6]=1[CH2:5][CH2:4][C:3]([OH:49])=[O:2])([OH:20])=[O:19]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The 2-[6-[[3,4-dihydro-4-oxo-8-(3-phenylpropyl)-2H-1-benzopyran-7-yl)oxy]hexyl]-6-[(6-methoxy-6-oxohexyl)oxy]benzenepropanoic acid methyl ester from the preceding example (0.38 g; 0.565 mmol) was saponified by stirring with 2 mL of 3N aqueous lithium hydroxide, in 15 mL of tetrahydrofuran for 24 hr, at room temperature. Work-up as in example 4 followed by flash-chromatography on silica gel (eluting with 96:3:1 chloroform-methanol-acetic acid) and recrystallization from hexane-ethyl acetate gave 0.36 g (98%) of the title compound as a colorless solid, mp 97°-98° C.
Workup
- customfollowed by flash-chromatography on silica gel (eluting with 96:3:1 chloroform-methanol-acetic acid) and recrystallization from hexane-ethyl acetate
Sources & evidence
- ORD record
- ord-7168de1e4fb2413ea637f527eb23aac7
- Source dataset
- uspto-grants-1993_12
- Patent number
- US05273999
Reaction notes
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