Triethylamine → HCID 89650387, compound

HRID 515945Notes

Reaction equation

HRID 515945 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[CH:22]=[CH:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:21]=[CH:22][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 1308945939825-33-7HCID 15936310HCID 15936310, compound

Product 1

HCID 89650387HCID 89650387, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

(S)-isopropyl 2-aminopropanoate hydrochloride (Oakwood, 500 mg, 2.98 mmol) and naphthalen-2-yl phosphorodichloridate (724 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 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-2-yloxy)phosphorylamino)propanoate as a light yellow oil (0.8 g, 75%) and used without further purification.

Workup

  1. temperatureto warmed 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-b1ee40ac1f434b18b18bd28bdfa3ec47
Source dataset
uspto-grants-2015_08
Patent number
US09108999B2

Reaction notes

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