Benzyl Alcohol → HCID 22789987, compound

HRID 1076285Notes

Reaction equation

HRID 1076285 reaction equation
FC[C@H](C(O)=O)N.O.[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([OH:18])(=[O:17])=[O:16])=[CH:11][CH:10]=1.C(O)C1C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[F:39][CH2:40][C@H:41]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[NH2:42]>N1C=CC=CC=1.C(O)(C)C.O.C1C=CC=CC=1>[C:9]1([CH3:19])[CH:10]=[CH:11][C:12]([S:15]([OH:18])(=[O:16])=[O:17])=[CH:13][CH:14]=1.[F:39][CH2:40][C@H:41]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[NH2:42].[F:39][CH2:40][C@H:41]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[NH2:42]

Participants

9

Reactant 4

HCID 244Benzyl AlcoholHCID 4397753-fluoro-D-alanineHCID 521998p-Toluenesulfonic acid monohydrateHCID 22789987HCID 22789987, compound

Product 2

HCID 22789987HCID 22789987, compoundHCID 22789988HCID 22789988, compound

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 962WaterSolventHCID 21074318HCID 21074318, compoundSolvent

Procedure

A mixture of 10.7 g. of 3-fluoro-D-alanine, 19.5 g. p-toluene sulfonic acid monohydrate, 50 ml. benzyl alcohol and 20 ml. benzene are heated at reflux temperature for a period of about 5 hours in an apparatus which continuously removes water formed in the reaction. The reaction solution is cooled, diluted with 200 ml. of ether, and the crystalline material which precipitates is recovered by filtration, washed with ether and dried to give about 10 g. of benzyl 3-fluoro-D-alaninate p-toluenesulfonate. Treatment of this benzyl 3-fluoro-D-alaninate p-toluenesulfonate with an aqueous-pyridine-isopropanol mixture gives benzyl 3-fluoro-D-alaninate.

Workup

  1. additionA mixture of 10.7 g
  2. customformed in the reaction
  3. temperatureThe reaction solution is cooled
  4. additiondiluted with 200 ml
  5. customof ether, and the crystalline material which precipitates
  6. filtrationis recovered by filtration
  7. washwashed with ether
  8. customdried
  9. customto give about 10 g

Sources & evidence

ORD record
ord-5c583e4f14ff4064a3d1eb402c8f020c
Source dataset
uspto-grants-1976_05
Patent number
US03956367

Reaction notes

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