Hydrochloric Acid → HCID 67354342, compound

HRID 75850Notes

Reaction equation

HRID 75850 reaction equation
[F:1][C:2]1[CH:33]=[CH:32][C:5]2[N:6]=[C:7]([O:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:20]=[C:19]([C:21]([NH:23][CH:24]([CH:29]([CH3:31])[CH3:30])[C:25]([O:27]C)=[O:26])=[O:22])[O:18][N:17]=4)=[CH:12][CH:11]=3)[S:8][C:4]=2[CH:3]=1.O.[OH-].[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:33]=[CH:32][C:5]2[N:6]=[C:7]([O:9][C:10]3[CH:11]=[CH:12][C:13]([C:16]4[CH:20]=[C:19]([C:21]([NH:23][CH:24]([CH:29]([CH3:31])[CH3:30])[C:25]([OH:27])=[O:26])=[O:22])[O:18][N:17]=4)=[CH:14][CH:15]=3)[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67353704Methyl 2-(3-(4-(6-fluorobenzo[d]thiazol-2-yloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate

Product 1

HCID 67354342HCID 67354342, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To Methyl 2-(3-(4-(6-fluorobenzo[d]thiazol-2-yloxy)phenyl)isoxazole-5-carboxamido)-3-methylbutanoate (160 mg) in THF (4 ml), 1 M aqueous solution of Lithium hydroxide monohydrate (0.68 ml) was added and reaction mixture was stirred at RT for 6 hours. The reaction mixture was acidified with dilute HCl and extracted with EtOAc. Organic layer was collected and dried over Na2SO4 and concentrated to obtain off white solid, which was crystallized from EtOAc to yield 82 mg (52%) of the title compound as white solid. MS (ES+): m/z 456 (M+1); 1HNMR (DMSO-d6, 300 MHz): δ 12.9 (bs, 1H), 9.04 (d, 1H), 8.08 (d, 2H), 7.93 (dd, 1H), 7.81 (s, 1H), 7.75 (dd, 1H), 7.67 (d, 2H), 7.3 (m, 1H), 4.29 (m, 1H), 2.23 (m, 1H), 0.96 (d, 6H).

Workup

  1. customreaction mixture
  2. extractionextracted with EtOAc
  3. customOrganic layer was collected
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto obtain off white solid, which
  7. customwas crystallized from EtOAc

Sources & evidence

ORD record
ord-cb05309ff0e0429a9659f9863d71dc6b
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Reaction notes

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