Hydrochloric Acid → (R)-2-Amino-1-(3-chlorophenyl)ethanol

HRID 1860318Notes

Reaction equation

HRID 1860318 reaction equation
[ClH:1].[NH2:2][CH2:3][CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[OH:5].[OH-].[Na+].N(C(OC(C)(C)C)=O)[C@H](C(O)=O)CC1C=CC(O)=CC=1>>[NH2:2][CH2:3][C@@H:4]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:1])[CH:7]=1)[OH:5]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1000PhenylethanolamineHCID 14798Sodium HydroxideHCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-

Product 1

HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanol

Procedure

To 15 ml of 1N aqueous solution of hydrochloric acid was added 3.38 g of the concentrate of the reaction products containing 15.0 mmol of 2-amino-1-phenylethanol obtained in the same manner as in Example 295. The resultant solution was added with 7.5 ml of 1N sodium hydroxide solution containing 2.10 g of Boc-L-Tyr (7.5 mmol) with stirring slowly to precipitate or crystallize crystals. The crystals were isolated by filtration to give 2.49 g (5.5 mmol) of (R)-2-amino-1-(3-chlorophenyl)ethanol.Boc-L-Tyr salt. The yield relative to (R)-2-amino-1-(3-chlorophenyl)ethanol in the concentrate was 73.4%.

Workup

  1. concentrationconcentrate of the reaction products
  2. customobtained in the same manner as in Example 295
  3. customto precipitate
  4. customcrystallize crystals
  5. customThe crystals were isolated by filtration

Sources & evidence

ORD record
ord-fc5a8b095f3e492086e6ee3706c0c1cd
Source dataset
uspto-grants-2003_03
Patent number
US06528686B1

Reaction notes

Loading…