Lithium hydroxide, monohydrate → HCID 25175638, compound

HRID 2190344Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:36])[N:9]([C:25]2[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=2)[C:28]([O:30]CC)=[O:29])[CH2:10][CH2:11][CH:12]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:4][C:3]=1[C:37]1[CH:42]=[CH:41][C:40]([NH:43][S:44]([CH3:47])(=[O:46])=[O:45])=[CH:39][CH:38]=1.O.[OH-].[Li+]>CO>[Cl:1][C:2]1[S:6][C:5]([NH:7][C:8]([N:9]([CH2:10][CH2:11][CH:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:26]=[C:27]([CH:33]=[CH:34][CH:35]=2)[C:28]([OH:30])=[O:29])=[O:36])=[N:4][C:3]=1[C:37]1[CH:38]=[CH:39][C:40]([NH:43][S:44]([CH3:47])(=[O:45])=[O:46])=[CH:41][CH:42]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 3-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)benzoate 73 (0.366 g, 0.531 mmol) in MeOH (20 mL) was added lithium hydroxide hydrate (0.440 g, 10.5 mmol). The reaction mixture was heated to 60° C. After 3 h, the reaction mixture was partially concentrated, neutralized with 1 M HCl, and diluted with EtOAc. The organic phase was washed with brine (1×), dried over MgSO4, filtered, and concentrated to give 3-(((5-chloro-4-(4-((methylsulfonyl)amino)phenyl)-1,3-thiazol-2-yl)carbamoyl)(3,3-diphenylpropyl)amino)benzoic acid 74. Mass spectrum, calculated for C33H29ClN4O5S2 660.1; found 661.1 (M++1).

Workup

concentrationthe reaction mixture was partially concentrated
additiondiluted with EtOAc
washThe organic phase was washed with brine (1×)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-ce4aaf72b855499b925ce6aad2c5ba37
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08324396B2

Reaction notes

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