Chloroform → HCID 69818081, compound

HRID 2417418Notes

Reaction equation

HRID 2417418 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@H:11]([NH:14][CH2:15][C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[OH:17])[CH2:12][OH:13])=[CH:6][CH:5]=1.C(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C@H:11]([NH:14][CH2:15][C@@H:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[OH:17])[CH2:12][OH:13])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 516892Sodium BicarbonateHCID 69818080HCID 69818080, compound

Product 1

HCID 69818081HCID 69818081, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of (2S)-3-(4-aminophenyl)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1-propanol dihydrochloride (3.68 g) in a mixed solvent of chloroform and methanol (9:1, 75 ml) was added a saturated aqueous sodium bicarbonate solution (75 ml) and the whole was stirred vigorously. The organic layer was separated and the aqueous layer was extracted with a mixed solvent of chloroform and methanol (9:1, 25 ml×5). The organic layers were combined, dried over magnesium sulfate, filtered, and evaporated to give (2S)-3-(4-aminophenyl)-2-[[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-1-propanol (2.78 g) as a pale orange crystalline solid.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with a mixed solvent of chloroform and methanol (9:1, 25 ml×5)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-ef4928c4dbc84347b9efa29a9d57b41b
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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