Lithium Hydroxide → (R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid

HRID 849835Notes

Reaction equation

HRID 849835 reaction equation
C[O:2][C:3](=[O:34])[C@H:4]([NH:16][C:17](=[O:33])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH:19]=1)[CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1.[OH-].[Li+].ClCCl.S([O-])(O)(=O)=O.[Na+]>CO.O>[C:29]([O:28][C:26]([NH:25][CH2:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[C:17]([NH:16][C@H:4]([CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=1)[C:3]([OH:34])=[O:2])=[O:33])=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 516919Sodium BisulfateHCID 53653839(R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid methyl ester

Product 1

HCID 54212651(R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(R)-2-(3-(tert-Butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid methyl ester (8.8 g, 19.1 mmol) was dissolved in methanol (100 ml) and lithium hydroxide (0.55 g, 22.2 mmol) was added. After 2 h dichloromethane (200 ml), water (200 ml) and 3 M sodium hydrogen sulfate (50 ml) were added. The organic phase was separated and washed with water (100 ml). The organic phase was dried (magnesium sulfate) and the solvent removed in vacuo to yield 7.9 g of (R)-2-(3-(tert-butoxycarbonylaminomethyl)benzoylamino)-3-(2-naphthyl)propionic acid.

Workup

  1. customThe organic phase was separated
  2. washwashed with water (100 ml)
  3. dry with materialThe organic phase was dried (magnesium sulfate)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-95a04fd314cc47bda0502ef1ab94c5e5
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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