Triethylamine → HCID 66713330, compound

HRID 515941Notes

Reaction equation

HRID 515941 reaction equation
[ClH:1].[NH2:2][C@@H:3]([CH3:10])[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5].[P:11](Cl)(Cl)(=[O:19])[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][P:11](=[N:2][C@@H:3]([CH3:10])[C:4]([O:6][CH:7]([CH3:9])[CH3:8])=[O:5])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 1308945939825-33-7

Product 1

HCID 66713330HCID 66713330, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(S)-isopropyl 2-aminopropanoate hydrochloride (Oakwood, 500 mg, 2.98 mmol) and phenyl phosphorodichloridate (Aldrich, 662 mg, 2.98 mmol) was suspended in anhydrous DCM (25 mL). The reaction was cooled to −78° C. Triethylamine (604 mg, 830 μl, 5.97 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, then allowed to warmed up to room temperature and stirred for overnight. The solvent was removed, the residue was washed with dry ether. The filtrate was concentrated to give crude (2S)-isopropyl 2-(chloro(phenoxy)phosphorylamino)propanoate as a light yellow oil (0.8 g, 88%) and used without further purification.

Workup

  1. temperatureto warmed up to room temperature
  2. stirringstirred for overnight
  3. customThe solvent was removed
  4. washthe residue was washed with dry ether
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-61dd4c56a62f4711852ffc435834f9a7
Source dataset
uspto-grants-2015_08
Patent number
US09108999B2

Reaction notes

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