Lithium Hydroxide → HCID 90418029, compound

HRID 2177293Notes

Reaction equation

HRID 2177293 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:26][CH2:27][C:28]([O:30]CC)=[O:29])[CH:5]=[C:6]([F:25])[C:7]=1[O:8][CH2:9][C:10]1[C:11]([O:23][CH3:24])=[N:12][S:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1.O1CCCC1.[Li+].[OH-]>O>[F:25][C:6]1[CH:5]=[C:4]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])[CH:3]=[C:2]([F:1])[C:7]=1[O:8][CH2:9][C:10]1[C:11]([O:23][CH3:24])=[N:12][S:13][C:14]=1[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90418625HCID 90418625, compound

Product 1

HCID 90418029HCID 90418029, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

Into a 25-mL round-bottom flask, was placed ethyl 3-(3,5-difluoro-4-[[3-methoxy-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methoxy]phenyl)propanoate (50 mg, 0.11 mmol, 1.00 equiv), tetrahydrofuran (3 mL), water (1 mL), LiOH (50 mg, 2.09 mmol, 19.30 equiv). The resulting solution was stirred overnight at 25° C. in an oil bath. The resulting mixture was concentrated under vacuum. The pH value of the solution was adjusted to 5 with hydrogen chloride (2 mol/L). The solids were collected by filtration, washed with n-hexane, dried. This resulted in 8.2 mg (17%) of 3-(3,5-difluoro-4-[[3-methoxy-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methoxy]phenyl) propanoic acid as a white solid. 1H NMR (300 MHz, CD3OD) δ7.53 (d, J=11.6 Hz, 2H), 7.05 (d, J=11.6 Hz, 2H), 6.81 (d, J=11.6 Hz, 2H), 5.16 (s, 2H), 4.06 (s, 3H), 3.92 (s, 3H), 2.88 (m, 2H), 2.71 (m, 2H). Mass spectrum (ESI, m/z): Calcd. for C21H19F2NO5S, 436.1 (M+H). found 436.0.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. filtrationThe solids were collected by filtration
  4. washwashed with n-hexane
  5. customdried
  6. customThis resulted in 8.2 mg (17%) of 3-(3,5-difluoro-4-[[3-methoxy-5-(4-methoxyphenyl)-1,2-thiazol-4-yl]methoxy]phenyl) propanoic acid as a white solid

Sources & evidence

ORD record
ord-37b86f8cca4a499ca2318928140fe992
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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