Sodium Hydroxide → 3-(2-(3-(Benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoic acid

HRID 1426180Notes

Reaction equation

HRID 1426180 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]([O:26]C)=[O:25])[N:21]=2)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C1COCC1.O>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:17]2[S:18][CH:19]=[C:20]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])[N:21]=2)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 16660673Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate

Product 1

HCID 592256873-(2-(3-(Benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoic acidYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoate (Example 58; 1.500 g, 3.346 mmol) was dissolved in THF (50 mL) and water (25 mL), followed by the addition of sodium hydroxide (0.2676 g, 6.691 mmol), and the mixture was at ambient temperature for 16 hours. The mixture was concentrated, and partitioned between DCM and saturated aqueous NH4Cl. The layers were separated and the aqueous was extracted with DCM/THF and then 100% THF. The combined organics were dried over Na2SO4, filtered and concentrated to give 3-(2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazol-4-yl)propanoic acid (1.42 g, 98% yield) as white solids. 1H NMR (DMSO-d6) δ 2.58 (t, J=7.6 Hz, 2H), 2.82 (t, J=7.6 Hz, 2H), 5.29 (s, 2H), 6.65 (s, 1H), 7.35 (t, J=7.2 Hz, 1H), 7.41 (t, J=7.2 Hz, 2H), 7.58 (s, 1H), 7.60 (s, 1H), 7.62 (d, J=2.0 Hz, 1H), 7.96 (d, J=1.8 Hz, 1H); Mass Spectrum (apci) 434 (M+H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between DCM and saturated aqueous NH4Cl
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with DCM/THF
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-87fbd109ce7b4bbd92841ed672b4ce61
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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