Triethylamine → Ethyl N-[chloro(4-chlorophenoxy)phosphoryl]-L-alaninate

HRID 1359935Notes

Reaction equation

HRID 1359935 reaction equation
[P:1]([Cl:12])(Cl)([O:3][C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][CH:5]=1)=[O:2].Cl.[CH2:14]([O:16][C:17](=[O:21])[C@H:18]([CH3:20])[NH2:19])[CH3:15].CCN(CC)CC>C(Cl)Cl>[Cl:12][P:1]([NH:19][C@H:18]([C:17]([O:16][CH2:14][CH3:15])=[O:21])[CH3:20])([O:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:10])=[CH:8][CH:9]=1)=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69879p-Chlorophenyl dichlorophosphateHCID 2724356L-Alanine, ethyl ester, hydrochloride (1:1)

Product 1

HCID 44226153Ethyl N-[chloro(4-chlorophenoxy)phosphoryl]-L-alaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described for Example 1, step 2, treatment of a solution in DCM (0.090 M) of 4-chlorophenyl 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* mixture of diastereoisomers.

Sources & evidence

ORD record
ord-3ddd7d4e011440eb9d7c77cc15a78b39
Source dataset
uspto-grants-2011_02
Patent number
US07879815B2

Reaction notes

Loading…