Sulfuric Acid → (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyridin-2-ylamino)-propanoic acid

HRID 55971Notes

Reaction equation

HRID 55971 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][N:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:10]([O-:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1([C@@H]([NH3+])C)C=CC=CC=1.S(=O)(=O)(O)O>C(O)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][N:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86692183(S)-1-Phenylethyl-ammonium (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyridin-2-ylamino)-propanoate

Product 1

HCID 56837165(S)-2-tert-butoxycarbonylamino-3-(phenyl-pyridin-2-ylamino)-propanoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of (S)-1-phenylethyl-ammonium (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyridin-2-ylamino)-propanoate (2.25 g, 4.69 mmol, 99.5% de) in aqueous isopropanol (50% strength, 6 ml) is admixed with 1N sulfuric acid (6 ml, 5.85 mmol) and stirred for 2 h at RT. The solid is filtered off with suction and dried to give (S)-2-tert-butoxycarbonylamino-3-(phenyl-pyridin-2-ylamino)-propanoic acid (1.35 g, 81%, >99.9% ee) as a colorless solid.

Workup

  1. filtrationThe solid is filtered off with suction
  2. customdried

Sources & evidence

ORD record
ord-494ec803fa71425498a2a52221a8e47a
Source dataset
uspto-grants-2016_09
Patent number
US09434696B2

Reaction notes

Loading…