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

HRID 1684889Notes

Reaction equation

HRID 1684889 reaction equation
P(Cl)(Cl)(O[P:4]([O-:14])([O:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)=O)=O.[ClH:17].[CH2:18]([O:25][C:26](=[O:30])[C@H:27]([CH3:29])[NH2:28])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CCN(CC)CC>C(Cl)Cl>[Cl:17][P:4]([NH:28][C@H:27]([C:26]([O:25][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:30])[CH3:29])([O:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 44225940L-alanine n-heptyl ester hydrochlorideHCID 86761540Para-chlorophenyl dichlorodiphosphate

Product 1

HCID 59157900n-Heptyl N-[chloro(4-chlorophenoxy)phosphoryl]-L-alaninate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure described for Step 1 of Example 1, treatment of a DCM (0.098 M) solution of para-chlorophenyl dichlorodiphosphate with L-alanine n-heptyl ester hydrochloride (1.0 eq.) and Et3N (2.0 eq.) provided the title compound as a colourless oil as a 1:1 mixture of diastereomers.

Sources & evidence

ORD record
ord-8230ae283f454ef5add18456644ec707
Source dataset
uspto-grants-2012_04
Patent number
US08148349B2

Reaction notes

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