L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl- → (R)-2-Amino-1-(3-chlorophenyl)ethanol

HRID 1860317Notes

Reaction equation

HRID 1860317 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].C(OC(N[C@H](C(O)=O)CC1C=CC(O)=CC=1)=O)(C)(C)C>C(O)CCC>[NH2:1][CH2:2][C@@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4]

Participants

4

Reactant 2

HCID 117439L-Tyrosine, N-(1,1-dimethylethoxy)carbonyl-2×HCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-ol

Product 1

HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanolYield 28.7%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent2×

Procedure

The concentrate (3.38 g) containing 15.0 mmol of 2-amino-1-(3-chlorophenyl)ethanol obtained in the same manner as in Example 295 was added to 20 ml of n-butanol and dissolved at 50° C. The mixture was added with 20 ml of n-butanol containing 2.10 g (7.5 mmol) of N-t-butoxycarbonyl-L-tyrosine (hereinafter briefly referred to as Boc-L-Tyr) with stirring slowly to separate crystals. After cooling to room temperature, the crystals were isolated by filtration to afford 1.95 g (4.31 mmol) of (R)-2-amino-1-(3-chlorophenyl)ethanol.Boc-L-Tyr salt. The yield based on the concentrate was 58.2%.

Workup

  1. concentrationThe concentrate (3.38 g)
  2. customobtained in the same manner as in Example 295
  3. dissolutiondissolved at 50° C
  4. customto separate crystals
  5. customthe crystals were isolated by filtration

Sources & evidence

ORD record
ord-05b6d2d4727f4d49832d4f03ec24cc8a
Source dataset
uspto-grants-2003_03
Patent number
US06528686B1

Reaction notes

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