Glycolic Acid → (R)-7-(2-(1-(4-butoxyphenyl)-2-methylpropan-2-ylamino)-1-hydroxyethyl)-5-hydroxybenzo[d]thiazol-2(3H)-one glycolate

HRID 1426884Notes

Reaction equation

HRID 1426884 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([NH:16][CH2:17][C@@H:18]([C:20]2[C:28]3[S:27][C:26](=[O:29])[NH:25][C:24]=3[CH:23]=[C:22]([OH:30])[CH:21]=2)[OH:19])([CH3:15])[CH3:14])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[C:31]([OH:35])(=[O:34])[CH2:32][OH:33]>C(#N)C.O>[C:31]([OH:35])(=[O:34])[CH2:32][OH:33].[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([NH:16][CH2:17][C@@H:18]([C:20]2[C:28]3[S:27][C:26](=[O:29])[NH:25][C:24]=3[CH:23]=[C:22]([OH:30])[CH:21]=2)[OH:19])([CH3:14])[CH3:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 757Glycolic AcidHCID 71294925(R)-7-(2-(1-(4-butoxyphenyl)-2-methylpropan-2-ylamino)-1-hydroxyethyl)-5-hydroxybenzo[d]thiazol-2(3H)-one

Product 1

HCID 71295007(R)-7-(2-(1-(4-butoxyphenyl)-2-methylpropan-2-ylamino)-1-hydroxyethyl)-5-hydroxybenzo[d]thiazol-2(3H)-one glycolate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

63.0 mg (0.146 mmol) of free base (R)-7-(2-(1-(4-butoxyphenyl)-2-methylpropan-2-ylamino)-1-hydroxyethyl)-5-hydroxybenzo[d]thiazol-2(3H)-one and 11.24 mg (0.146 mmol) glycolic acid were dissolved in 1.0 ml acetonitrile and 0.05 ml water. The solution was stirred at r.t. with a magnetic stirrer. Precipitation took place overnight. The suspension was filtered at r.t. through a glass filter and washed three times with 0.5 ml acetonitrile. The wet filter cake was dried in a drying oven overnight (16 h) at r.t. to dryness. Yield: 52 mg white powder

Workup

  1. customPrecipitation
  2. customplace overnight
  3. filtrationThe suspension was filtered at r.t. through a glass
  4. filtrationfilter
  5. washwashed three times with 0.5 ml acetonitrile
  6. customThe wet filter cake was dried in a drying oven overnight (16 h) at r.t. to dryness

Sources & evidence

ORD record
ord-6a18512693ec4a68ae5d2d7b643a4c27
Source dataset
uspto-grants-2015_01
Patent number
US08933108B2

Reaction notes

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