(R)-camphorsulfonic acid → HCID 86745525, compound

HRID 2371490Notes

Reaction equation

HRID 2371490 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH:21]([N:23](C1CCCCO1)[OH:24])[CH3:22].[C@@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH:21]([NH:23][OH:24])[CH3:22]

Participants

4

Reactant 2

HCID 131278(R)-camphorsulfonic acidHCID 86745526HCID 86745526, compound

Product 1

HCID 86745525HCID 86745525, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The amine intermediate from Step 2 was heated to 50° C. in methanol (20 mL) containing (1R)-(-)-10-camphorsulfonic acid (200 mg) for 18 hours. After quenching with brine the mixture was extracted with ether (100 mL). The crude material was chromatographed on silica gel eluting with a 1:5 mixture of ethyl acetate-hexane to collect the least polar of the two main components of the mixture. This afforded the title compound as a yellow filmy residue which was taken into the next step.

Workup

  1. customAfter quenching with brine the mixture
  2. extractionwas extracted with ether (100 mL)
  3. customThe crude material was chromatographed on silica gel eluting with a 1:5 mixture of ethyl acetate-hexane
  4. customto collect the least polar of the two main components of the mixture

Sources & evidence

ORD record
ord-4283e7ef141045f49ad57de5a7803e4a
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Reaction notes

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