Reaction #1447113

ord-7ba21c1a7b934bf3b41ff8466da5e769

Reaction equation

O=P(Cl)(Cl)Oc1cccc2ccccc12
1-naphthyl dichlorophosphate
CCOC(=O)[C@H](C)N.Cl
L-alanine ethyl ester hydrochloride
CCN(CC)CC
Et3N
→
CCOC(=O)[C@H](C)NP(=O)(Cl)Oc1cccc2ccccc12
title compound
CCOC(=O)[C@H](C)NP(=O)(Cl)Oc1cccc2ccccc12
Ethyl N-[chloro(1-naphthyloxy)phosphoryl]-L-alaninate

Reactants

O=P(Cl)(Cl)Oc1cccc2ccccc12
1-naphthyl dichlorophosphate
CCOC(=O)[C@H](C)N.Cl
L-alanine ethyl ester hydrochloride
CCN(CC)CC
Et3N

Reagents

None

Solvents

ClCCl
DCM

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Following the procedure described for Example 1, step 2, treatment of a solution in DCM (0.144 M) of 1-naphthyl dichlorophosphate with L-alanine ethyl ester hydrochloride (1.0 eq.) and Et3N (2.0 eq.) provided the title compound as a colorless oil as a 1:1.1* mixture of diastereoisomers. 31P NMR (300 MHz, CDCl3) δ: 9.47 and 9.14*.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07879815B2uspto-grants-2011_02