Oxalyl chloride → HCID 10026851, compound

HRID 1446424Notes

Reaction equation

HRID 1446424 reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([OH:13])=O.C(Cl)(=O)C(Cl)=O.Cl.[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][CH:34]=2)[CH:29]([NH2:31])[CH3:30])=[CH:24][CH:23]=1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.CN(C)C=O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([Cl:39])=[CH:37][CH:38]=2)[CH:29]([NH:31][C:11]([CH:2]2[CH2:3][CH2:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH2:1]2)=[O:13])[CH3:30])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 1013701,2,3,4-Tetrahydro-2-naphthoic acidHCID 222704272,3-Bis(4-chlorophenyl)-1-methylpropylamine hydrochloride

Product 1

HCID 10026851HCID 10026851, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,2,3,4-tetrahydro-2-naphthoic acid (Aldrich, 0.50 g, 2.8 mmol) in methylene chloride (10 mL) at 0° C. was added a drop of dimethylformamide and oxalyl chloride (2 M in methylene chloride, 4.3 mL, 8.5 mmol). After stirring at room temperature for 2 h, the reaction mixture was concentrated on a rotary evaporator and dried under vacuum, and the resulting crude acyl chloride (0.55 g) was used without further purification. Thus, the crude acyl chloride (88 mg, 0.45 mmol) was dissolved in 1 mL of methylene chloride and was added 3,4-bis(4-chlorophenyl)-1-methylpropyl-amine hydrochloride salt (Reference Example 1) (Diastereomer α, 0.10 g, 0.30 mmol) and diisopropylethylamine (0.16 mL, 0.91 mmol). After stirring at room temperature for 6 h, the reaction mixture was loaded onto a silica gel column, which was eluted with 10% ethyl acetate to give a faster eluting diastereomer (Diastereomer I) and a slower eluting diastereomer (Diastereomer II) along with some mixed fractions.

Workup

  1. concentrationthe reaction mixture was concentrated on a rotary evaporator
  2. customdried under vacuum
  3. customthe resulting crude acyl chloride (0.55 g) was used without further purification
  4. stirringAfter stirring at room temperature for 6 h
  5. washwas eluted with 10% ethyl acetate
  6. customto give
  7. washa faster eluting diastereomer (Diastereomer I)
  8. washa slower eluting diastereomer (Diastereomer II) along with some mixed fractions

Sources & evidence

ORD record
ord-1f87624d07244d6790e6481f8bf7a092
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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