Hexane → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1(R)-(3-chlorophenyl)ethanol fumarate

HRID 1682730Notes

Reaction equation

HRID 1682730 reaction equation
CCCCCC.[CH3:7][O:8][C:9]([CH2:11][C:12]1[CH:32]=[CH:31][C:15]([O:16][CH2:17][C@H:18]([NH:20][CH2:21][C@@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[OH:23])[CH3:19])=[CH:14][CH:13]=1)=[O:10].[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37]>C(OCC)(=O)C>[C:33]([OH:40])(=[O:39])/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37].[CH3:7][O:8][C:9]([CH2:11][C:12]1[CH:32]=[CH:31][C:15]([O:16][CH2:17][C@H:18]([NH:20][CH2:21][C@@H:22]([C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=2)[OH:23])[CH3:19])=[CH:14][CH:13]=1)=[O:10]

Participants

5

Reactant 3

HCID 8058HexaneHCID 444972Fumaric AcidHCID 228670762-[2-(4-methoxycarbonylmethylphenoxy)-1(R)methylethyl]amino-1(R)-(3-chlorophenyl)ethanol

Product 1

HCID 228731262-[2-(4-Methoxycarbonylmethylphenoxy)-1(R)-methylethyl]amino-1(R)-(3-chlorophenyl)ethanol fumarateYield 93.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

30 ml of hexane were slowly added to a solution of 1.6 g of 2-[2-(4-methoxycarbonylmethylphenoxy)-1(R)methylethyl]amino-1(R)-(3-chlorophenyl)ethanol (prepared as described in Example 46) and 491 mg of fumaric acid in 5 ml of ethyl acetate, whilst irradiating the reaction mixture with ultrasonic waves. The crystals which precipitated were collected by filtration and dried, to give 1.95 g of the title compound as crystals, melting at 73°-78° C. [α]D23 -19.4° (c=1.01, methanol).

Workup

  1. customwhilst irradiating the reaction mixture with ultrasonic waves
  2. customThe crystals which precipitated
  3. filtrationwere collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-719a3e26b8a8497c8557909e3baff067
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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