Sodium Hydroxide → HCID 45110931, compound

HRID 468588Notes

Reaction equation

HRID 468588 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([C@H:15]([CH3:19])[C:16]([OH:18])=[O:17])=[CH:11][CH:10]=2)[S:6][CH:7]=1.[OH-].[Na+:23]>O>[F:21][C:2]([F:1])([F:20])[C:3]1[N:4]=[C:5]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([C@H:15]([CH3:19])[C:16]([O-:18])=[O:17])=[CH:13][CH:14]=2)[S:6][CH:7]=1.[Na+:23]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 45110932HCID 45110932, compound

Product 1

HCID 45110931HCID 45110931, compoundYield 96.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 100 ml round-bottomed flask equipped with a magnetic stirrer, compound 3 (7.26 gr, 22.9 mmol) was suspended in water (30 ml) and 2N NaOH (11.45 ml, 22.9 mol) was slowly added. The resulting dark red solution was stirred for 1 h at room temperature, filtered on a 0.45μ filter and freeze dried. Pure sodium (2S)-2-(4-{[4-(trifluoromethyl)-1,3-thiazol-2-yl]amino}phenyl)propanoate 3a (7.51 g, 22.2 mmol) was obtained as white solid (97%). m.p. 142°-145° C. [α]D=−8.7 (c=0.62; CH3OH); 1H-NMR (D2O): δ 9.00 (bs, 1H, NH), 7.30 (m, 4H), 7.28 (s, 1H), 3.55 (q, 1H, J=7 Hz), 1.35 (d, 3H, J=7 Hz).

Workup

  1. customIn a 100 ml round-bottomed flask equipped with a magnetic stirrer
  2. filtrationfiltered on a 0.45μ
  3. filtrationfilter
  4. customfreeze dried

Sources & evidence

ORD record
ord-aa437b4425b64c488a535d46f3fb0824
Source dataset
uspto-grants-2014_01
Patent number
US08624036B2

Reaction notes

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