Hydrochloric Acid → HCID 52934821, compound

HRID 1024448Notes

Reaction equation

HRID 1024448 reaction equation
[C:1]([C:5]1[CH:35]=[CH:34][C:8]([C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:22][C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:33])[CH3:32])[C:27]([O:29]C)=[O:28])=[O:24])=[N:20][CH:19]=3)=[CH:14][CH:13]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O.[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:35]=[CH:34][C:8]([C:9]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]3[S:22][C:21]([C:23]([NH:25][CH:26]([CH:31]([CH3:32])[CH3:33])[C:27]([OH:29])=[O:28])=[O:24])=[N:20][CH:19]=3)=[CH:16][CH:17]=2)=[O:10])=[CH:7][CH:6]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 52934822HCID 52934822, compound

Product 1

HCID 52934821HCID 52934821, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-(5-(4-(4-tert-butylbenzamido)phenyl)thiazole-2-carboxamido)-3-methylbutanoate (110 mg) in THF (2.2 ml) was added 1 M aqueous solution of Lithium hydroxide monohydrate (0.44 ml) and the reaction mixture was stirred at RT for 4 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. The organic layer was separated, dried over Na2SO4, concentrated under vacuum to get off white solid which was crystallized in EtOAc to give the title compound. Yield: 87 mg (81%); 1H NMR (DMSO-d6, 300 MHz): δ 13.02 (bs, 1H), 10.38 (s, 1H), 8.4 (s, 1H), 8.36 (d, 1H), 7.94 (d, 2H), 7.91 (d, 2H), 7.8 (d, 2H), 7.58 (d, 2H), 4.32 (m, 1H), 2.26 (m, 1H), 0.95 (d, 6H); MS (ES+) m/z 480 (M+1).

Workup

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customto get off white solid which
  6. customwas crystallized in EtOAc

Sources & evidence

ORD record
ord-69e323427b4b48bcaa0d2996d76f7e81
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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