Sodium Hydroxide → HCID 49806576, compound

HRID 1627931Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[C:16]([Cl:25])=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH2:20][CH2:19][CH2:18]3)[C:3]=1[CH:26]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:27]([O:29]C)=[O:28].[OH-].[Na+]>CO>[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:5]2=[C:4]([C:15]2[C:16]([Cl:25])=[C:17]3[C:22](=[CH:23][CH:24]=2)[O:21][CH2:20][CH2:19][CH2:18]3)[C:3]=1[CH:26]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[C:27]([OH:29])=[O:28]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of Methyl 2-[2-methyl-4-(5-chlorochroman-6-yl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-3-yl]-2-tert-butoxyacetate (0.027 g; 0.053 mmol) in methanol (0.9 mL) was added a solution of sodium hydroxide 10 N (0.090 mL; 0.90 mmol) and the mixture was heated to 60° C. for 18 h. The volatiles were removed under reduced pressure and the residue was dissolved in water, the mixture was then acidified by adding 1N HCl until a precipitate was formed. The solid was filtered, washed with water and dried under reduced pressure. Purification by preparative HPLC (HPLC method 1) furnished 0.005 g (18%) of the title compound as a white solid.

Workup

customThe volatiles were removed under reduced pressure
dissolutionthe residue was dissolved in water
additionby adding 1N HCl until a precipitate
customwas formed
filtrationThe solid was filtered
washwashed with water
customdried under reduced pressure
customPurification by preparative HPLC (HPLC method 1)

Sources & evidence

ORD record: ord-3b5368a10eb145e18806056d1aa4561e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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