Phosphorodichloridic acid, phenyl ester → HCID 66687284, compound

HRID 1425683Notes

Reaction equation

HRID 1425683 reaction equation
[C:1]1([O:7][P:8](Cl)(Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:12].[NH2:13][C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH3:18])=[O:16].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[Cl:12][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[O:7][P:8](=[N:13][C:14]([CH3:20])([CH3:19])[C:15]([O:17][CH3:18])=[O:16])=[O:9]

Participants

5

Reactant 3

HCID 13038Phosphorodichloridic acid, phenyl esterHCID 81531DiisopropylethylamineHCID 13258034Methyl 2-aminoisobutyrate hydrochloride

Product 1

HCID 66687284HCID 66687284, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of phenylphosphorodichloridate (1.0 eq., 13.0 mmol, 1.9 mL) and methyl α-aminoisobutyrate hydrochloride (1.0 eq., 13.0 mmol, 2.0 g) in CH2Cl2 (80 mL) was cooled to −80° C. Dry N, N-diisopropylethylamine (DIPEA; 2.0 eq., 26.0 mmol, 4.3 mL) was added dropwise. After 2 hours, the reaction was warmed to room temperature and the solvent was removed under reduced pressure. Dry diethylether was added and the precipitate was filtered off and washed twice with dry diethylether under an argon atmosphere. The filtrate was evaporated to dryness to give 11 which was stored as a 0.90 M solution in dry tetrahydrofuran (THF) at −18° C.

Workup

  1. customthe solvent was removed under reduced pressure
  2. additionDry diethylether was added
  3. filtrationthe precipitate was filtered off
  4. washwashed twice with dry diethylether under an argon atmosphere
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-ec1434a982f34568b33464d3a189002d
Source dataset
uspto-grants-2015_01
Patent number
US08933052B2

Reaction notes

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