phenylalaninol, (S)- → HCID 20666641, compound

HRID 1068851Notes

Reaction equation

HRID 1068851 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](Cl)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:17][C@@H:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:19][OH:20]>C(Cl)Cl.[OH-].[Na+]>[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10]([NH:17][C@@H:18]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:19][OH:20])=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 447213phenylalaninol, (S)-HCID 126823622-Benzylbenzoyl chloride

Product 1

HCID 20666641HCID 20666641, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

At 0° C., 2.1 g (9.2 mmol) of 2-benzylbenzoyl chloride dissolved in a little methylene chloride were added dropwise to 1.3 g (8.6 mmol) of (S)-2-amino-3-phenylpropan-1-ol in 35 ml of methylene chloride and 20 ml of 2M aqueous sodium hydroxide solution. The mixture was stirred for about 30 min. The organic phase was separated off, dried and concentrated under reduced pressure. 2.7 g (91%) of the product were obtained.

Workup

  1. customThe organic phase was separated off
  2. customdried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-957f9536807f4267b177eb81ed67a701
Source dataset
uspto-grants-2001_06
Patent number
US06251917B1

Reaction notes

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