Acetic Acid → N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-phenyl-thiazol-4-yl)ethanamine

HRID 477098Notes

Reaction equation

HRID 477098 reaction equation
[OH:1][CH:2]([C:5]1[N:6]=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[S:8][CH:9]=1)[CH2:3][NH2:4].[C:16]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29](=O)[CH3:30])=[CH:24][CH:23]=1)([O:18][CH3:19])=[O:17].C(O)(=O)C.C([BH3-])#N.[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[C:16]([CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:28][CH:29]([NH:4][CH2:3][CH:2]([OH:1])[C:5]2[N:6]=[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:8][CH:9]=2)[CH3:30])=[CH:26][CH:27]=1)([O:18][CH3:19])=[O:17]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetateHCID 140762412-Hydroxy-2-(2-phenyl-thiazol-4-yl)ethanamine

Product 1

HCID 19974288N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-phenyl-thiazol-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.32 g (0.006 mol) of 2-Hydroxy-2-(2-phenyl-thiazol-4-yl)ethanamine and 1.33 g (0.006 mol) of 1-(4-carbomethoxymethoxyphenyl)-propan-2-one are dissolved in 40 ml of absolute methanol, and 0.34 ml (0.006 mol) of glacial acetic acid and 0.37 g (0.006 mol) of sodium cyanoborohydride are added and the mixture is stirred at room temperature for 20 hours. It is then poured onto ice, and the mixture is acidified with hydrochloric acid, made alkaline with sodium bicarbonate solution and extracted with chloroform. The extract is dried over sodium sulphate, concentrated and purified on a silica gel column using ethyl acetate/methanol=9:1 as eluant.

Workup

  1. additionIt is then poured onto ice
  2. extractionextracted with chloroform
  3. dry with materialThe extract is dried over sodium sulphate
  4. concentrationconcentrated
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-de617bdea5384b2990c768a19eaa1a7d
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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