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

HRID 29766Notes

Reaction equation

HRID 29766 reaction equation
C([O:3][C:4](=[O:34])[CH:5]([CH2:19][C:20]1[CH:21]=[N:22][C:23]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:24][CH:25]=1)[CH2:6][P:7]([OH:18])([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])C.[Li+].[OH-].C(OC(=O)C)C>CC#N.O>[C:30]([O:29][C:27]([NH:26][C:23]1[N:22]=[CH:21][C:20]([CH2:19][CH:5]([CH2:6][P:7]([OH:18])([CH2:9][CH2:10][CH2:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:8])[C:4]([OH:34])=[O:3])=[CH:25][CH:24]=1)=[O:28])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 541967722-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl ester

Product 1

HCID 544678532-(6-Tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acidYield 77%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid ethyl ester (0.240 g 0.489 mmol) in MeCN (3 mL) was added a solution of LiOH (0.059 g 2.45 mmol) in H2O (3 mL). The mixture was then stirred at 20° C. for 1.5 hours. Ethylacetate was added and the mixture was washed with 1 M HCL and brine and filtered to give 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-3-[hydroxy-(3-phenyl-propyl)-phosphinoyl]-propionic acid (0.174 g, 77%) as white crystals.

Workup

  1. washthe mixture was washed with 1 M HCL and brine
  2. filtrationfiltered

Sources & evidence

ORD record
ord-9e2e4b3a3492493ba76bc8a8211a2864
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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