Methanol → HCID 54765463, compound

HRID 1844765Notes

Reaction equation

HRID 1844765 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C@@H:13]2[CH2:17][CH2:16][C@H:15]([NH:18][C@@H:19]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[CH3:20])[CH2:14]2)=[CH:9][CH:8]=1)C.CO.[Li+].[OH-]>O>[C:21]1([C@H:19]([NH:18][C@H:15]2[CH2:16][CH2:17][C@@H:13]([C:10]3[CH:9]=[CH:8][C:7]([O:6][CH2:5][C:4]([OH:31])=[O:3])=[CH:12][CH:11]=3)[CH2:14]2)[CH3:20])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 59617257HCID 59617257, compound

Product 1

HCID 54765463HCID 54765463, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

{4-[(1R,3S)-3-((R)-1-naphthalen-1-yl-ethylamino)-cyclopentyl]-phenoxy}-acetic acid ethyl ester (0.214 g, 0.51 mmol) was added to a mixture of methanol (2.35 ml) and water (0.78 ml). To the milk-white mixture was added aqueous 2N LiOH (2.05 ml, 4.1 mmol). After stirring for about 10 minutes at room temperature the reaction mixture changed into a clear light yellow solution. The solution was stirred overnight at room temperature. After 20 hours the solution was concentrated slightly in vacuo and further 5 ml of water was added. The product was precipitated by adding 4N HCl (2.4 ml) under vigorous stirring. pH was adjusted to 5 with aqueous 2N LiOH. The precipitate was collected by filtration to give crude amorphous {4-[(1R,3S)-3-((R)-1-naphthalen-1-yl-ethylamino)-cyclopentyl]phenoxy}-acetic acid. Yield: 0.19 g (95%).

Workup

  1. stirringThe solution was stirred overnight at room temperature
  2. concentrationAfter 20 hours the solution was concentrated slightly in vacuo and further 5 ml of water
  3. additionwas added
  4. customThe product was precipitated
  5. additionby adding 4N HCl (2.4 ml) under vigorous stirring
  6. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-62bb95bd9a5d4298b24e2869ec61c697
Source dataset
uspto-grants-2015_02
Patent number
US08946474B2

Reaction notes

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