Triethylamine → N-((R)-methylphenylphosphinyl)-N-hexyl-D-alanine methyl ester

HRID 355456Notes

Reaction equation

HRID 355456 reaction equation
[CH3:1][P:2](Cl)([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].[CH3:11][O:12][C:13](=[O:23])[C@@H:14]([CH3:22])[NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(N(CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[CH3:11][O:12][C:13](=[O:23])[C@@H:14]([CH3:22])[N:15]([P@@:2]([CH3:1])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 21983Methyl(phenyl)phosphinoyl chlorideHCID 53973081N-hexyl-D-alanine methyl ester

Product 1

HCID 10496278N-((R)-methylphenylphosphinyl)-N-hexyl-D-alanine methyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methylphenyl-phosphinic chloride (1.05 g, 6 mmol) is dissolved in dichloromethane (50 mL) and cooled to 0° C. To this is added a solution of N-hexyl-D-alanine methyl ester (1 g, 5.34 mmol) and triethylamine (2.1 mL, 15 mmol) in dichloromethane (10 mL). A catalytic amount of 4-dimethylaminopyridine is added and reaction is stirred for 16 hours, washed with water and brine, dried over sodium sulfate, and concentrated. The crude product is purified by silica gel flash chromatography (100% ethyl acetate) to give N-((R)-methylphenylphosphinyl)-N-hexyl-D-alanine methyl ester as an oil.

Workup

  1. customreaction
  2. washwashed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe crude product is purified by silica gel flash chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-cc36f5194f6540fea9b4b7ee54f690b9
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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