2-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid → 2-(6-Amino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid

HRID 899069Notes

Reaction equation

HRID 899069 reaction equation
C(OC([NH:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16]([CH2:20][P:21]([OH:32])([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1)=O)(C)(C)C>C(OC(=O)C)C>[NH2:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][CH:16]([CH2:20][P:21]([OH:32])([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)=[O:22])[C:17]([OH:19])=[O:18])=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 544678532-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid

Product 1

HCID 693029902-(6-Amino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acidYield 93.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid (0.170 g, 0.367 mmol) in ethylacetate (3 mL) at 4° C. was slowly added ethylacetate (4 mL. saturated with HCl(g)). The mixture was then stirred for 22 h. Concentration under reduced pressure gave the title compound (0.124 g, 93%) as the hydrochloride salt.

Workup

  1. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-3258a7b288774a188b653885ac524552
Source dataset
uspto-grants-2008_04
Patent number
US07354895B1

Reaction notes

Loading…