Tetrahydrofuran → HCID 86661959, compound

HRID 705156Notes

Reaction equation

HRID 705156 reaction equation
Cl[P:2]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])(Cl)=[O:3].[ClH:18].[CH3:19][O:20][C:21](=[O:25])[C@H:22]([CH3:24])[NH2:23].[CH2:26](N(CC)CC)C.C1COCC1>ClCCl>[Cl:18][C:8]1[C:7]([CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][P:2](=[N:23][C@H:22]([CH3:24])[C:21]([O:20][CH2:19][CH3:26])=[O:25])=[O:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 2733257Alanine methyl ester hydrochlorideHCID 86661958Methyl 3-(2-(dichlorophosphoryloxy)phenyl)propanoate

Product 1

HCID 86661959HCID 86661959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 3-(2-(dichlorophosphoryloxy)phenyl)propanoate, 81 (2.77 mmol) and L-alanine methyl ester hydrochloride (0.42 g, 2.77 mmol) were suspended in anhydrous dichloromethane (10 mL). Anhydrous triethylamine (0.37 mL, 2.77 mmol) and dichloromethane (5 mL) were added dropwise at −78° C. under nitrogen. Following the addition, the reaction mixture was slowly warmed to rt and stirred overnight. The solvent was removed under reduced pressure; the solid was washed with anhydrous ether (20 mL×2), and filtered. The filtrate was concentrated to a residue to give crude product as an oil. Dilution with THF (2.77 mL) gave a 1 M solution, which was used in the following step without any further purification.

Workup

  1. additionthe addition
  2. customThe solvent was removed under reduced pressure
  3. washthe solid was washed with anhydrous ether (20 mL×2)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated to a residue
  6. customto give crude product as an oil

Sources & evidence

ORD record
ord-6461650eb9d2411eb78ab7f2a2d4a455
Source dataset
uspto-grants-2015_11
Patent number
US09173893B2

Reaction notes

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