(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acid → (S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acid

HRID 280918Notes

Reaction equation

HRID 280918 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]([C:21]([OH:23])=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.[H][H]>CO.[C].[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][CH2:11][C@@H:12]([C:21]([OH:23])=[O:22])[NH:13][C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

5

Reactant 2

HCID 18599736(S)-2-((tert-butoxycarbonyl)amino)-3-(2-nitrophenoxy)propanoic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 18599735(S)-3-(2-aminophenoxy)-2-((tert-butoxycarbonyl)amino)propanoic acidYield 84.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In 500 ml of methanol is dissolved 30 g of O-(o-nitrophenyl)-Boc-L-serine obtained in Example 1, and catalytic reduction is conducted in a stream of hydrogen at ordinary temperature and at atmospheric pressure with 1 g of 10% palladium-carbon used as a catalyst. The catalyst is filtered off, and the filtrate is concentrated under reduced pressure. The resulting residue is recrystallized from ethyl acetate to give 23 g of O-(o-aminophenyl)-Boc-L-serine as colorless crystals, melting at 90°-91° C.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e25c6ff3e93d47129768902c2dc944cb
Source dataset
uspto-grants-1986_05
Patent number
US04591458

Reaction notes

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