Sodium Hydroxide → E-3030 trihydrate

HRID 1160479Notes

Reaction equation

[OH2:1].O.[Cl-].[Ca+2:4].[Cl-].[Cl:6][C:7]1[CH:33]=[CH:32][C:10]([O:11][CH2:12][C@@H:13]([F:31])[CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH2:22][C@H:23]([O:27][CH:28]([CH3:30])[CH3:29])[C:24]([OH:26])=[O:25])[CH:19]=[CH:20][CH:21]=2)=[C:9]([C:34]#[N:35])[CH:8]=1.[OH-].[Na+]>O.CO.CC(C)=O>[OH2:11].[OH2:1].[OH2:11].[Cl:6][C:7]1[CH:33]=[CH:32][C:10]([O:11][CH2:12][C@@H:13]([F:31])[CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH2:22][C@H:23]([O:27][CH:28]([CH3:30])[CH3:29])[C:24]([O-:26])=[O:25])[CH:19]=[CH:20][CH:21]=2)=[C:9]([C:34]#[N:35])[CH:8]=1.[Cl:6][C:7]1[CH:33]=[CH:32][C:10]([O:11][CH2:12][C@@H:13]([F:31])[CH2:14][O:15][C:16]2[CH:17]=[C:18]([CH2:22][C@H:23]([O:27][CH:28]([CH3:30])[CH3:29])[C:24]([O-:26])=[O:25])[CH:19]=[CH:20][CH:21]=2)=[C:9]([C:34]#[N:35])[CH:8]=1.[Ca+2:4]

Participants

Conditions

Temperature: 15 °C

Procedure

A methanol solution (500 mL) of calcium chloride dihydrate (23.8 g, 0.16 mol) was added to an acetone (1750 mL) solution of (2S)-3-[3-[(2S)-3-(4-chloro-2-cyanophenoxy)-2-fluoropropoxy]phenyl]-2-isopropoxypropionic acid (140 g, 0.32 mol) at 40° C. After confirming the dissolution, methanol (1,250 mL) was added to the reaction mixture. The reaction mixture was heated to 40° C., to which a 5N sodium hydroxide aqueous solution (64 mL, 0.32 mol) was then added dropwise over a period of 8 minutes and then water (134 ml) was added dropwise over a period of 29 minutes. The reaction mixture was cooled to 15° C., followed by filtering the precipitated crystal before vacuum drying at 40° C. to obtain 136.5 g of the title compound (yield: 93%).

Workup

additionwas added to the reaction mixture
additionwas then added dropwise over a period of 8 minutes
filtrationby filtering the precipitated crystal before vacuum
customdrying at 40° C.

Sources & evidence

ORD record: ord-7b9ebe41d254420e97b2ae0899a74cd5
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816405B2

Reaction notes

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