Triethylamine → HCID 66779574, compound

HRID 515943Notes

Reaction equation

HRID 515943 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:23])[O:12][C:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:14]1[CH:15]=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[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:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5756311-DichlorophosphoryloxynaphthaleneHCID 1308945939825-33-7

Product 1

HCID 66779574HCID 66779574, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(S)-isopropyl 2-aminopropanoate hydrochloride (Oakwood, 1.28 g, 7.64 mmol) and naphthalen-1-yl phosphorodichloridate (2 g, 7.66 mmol) was suspended in anhydrous DCM (35 mL). The reaction was cooled to −78° C. Triethylamine (1.55 g, 2.13 mL, 15.3 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 1 h, then warmed up to room temperature and stirred for 5 h. The solvent was removed, and the residue was washed with dry ethyl ether and filtered. The filtrate was concentrated to give crude (2S)-isopropyl 2-(chloro(naphthalen-1-yloxy)phosphorylamino)propanoate as a light yellow oil (2.5 g, 92%) and used without further purification.

Workup

  1. temperaturewarmed up to room temperature
  2. stirringstirred for 5 h
  3. customThe solvent was removed
  4. washthe residue was washed with dry ethyl ether
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-37273bec7e8142938fa0e975d45921d9
Source dataset
uspto-grants-2015_08
Patent number
US09108999B2

Reaction notes

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