Benzyl Alcohol → Benzyl (2r)-2-amino-2-cyclohexylethanoate methanesulfonate

HRID 1059086Notes

Reaction equation

HRID 1059086 reaction equation
[NH2:1][C@H:2]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]([OH:5])=[O:4].[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].O>C1(C)C=CC=CC=1.C(OC)(C)(C)C>[CH3:20][S:21]([OH:24])(=[O:23])=[O:22].[NH2:1][C@H:2]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)[C:3]([O:5][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:4]

Participants

7

Reactant 4

HCID 244Benzyl Alcohol2×HCID 962Water2×HCID 6395Methanesulfonic AcidHCID 736849Cyclohexylglycine, (R)-

Product 1

HCID 131723768Benzyl (2r)-2-amino-2-cyclohexylethanoate methanesulfonateYield 92%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To a suspension of (2R)-2-amino-2-cyclohexylethanoic acid (200 g, 1.27 mol) and benzyl alcohol (276 g, 2.54 mol) in toluene (1600 mL) was added methanesulphonic acid at a rate which did not allow the temperature to reach 100° C. The reaction was stirred for an additional six hours at between 110 and 115° C. The water that was produced was distilled off using a Dean-Stark trap. An additional portion of benzyl alcohol (276 g, 2.54 mol) was added and the mixture was refluxed for a further twelve hours with water distillation. The reaction mixture was then cooled and methyl tert-butyl ether was added to initiate crystallisation. The product was filtered and dried to yield 404 g (92%) of the sub-title compound.

Workup

  1. customto reach 100° C
  2. distillationwas distilled off
  3. temperatureThe reaction mixture was then cooled
  4. customcrystallisation
  5. filtrationThe product was filtered
  6. customdried

Sources & evidence

ORD record
ord-e8cf7fbc71bf434a9f0b49cd08164f74
Source dataset
uspto-grants-2003_02
Patent number
US06518434B2

Reaction notes

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