Diethylamine → HCID 58786731, compound

HRID 1376035Notes

Reaction equation

HRID 1376035 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22](O)=[O:23])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(P(=O)(OCC)OCC)#N.[CH2:35]([NH:37][CH2:38][CH3:39])[CH3:36]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([C:22](=[O:23])[N:37]([CH2:38][CH3:39])[CH2:35][CH3:36])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 76257Diethyl cyanophosphonateHCID 27622272-(2-methylphenyl)-2-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]acetic Acid

Product 1

HCID 58786731HCID 58786731, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 4-(Carboxy-o-tolyl-methyl)-piperazine-1-carboxylic acid tert-butyl ester (352) (0.654 g, 1.95 mmol) in DMF (5 mL) was added diethyl cyanophosphonate (0.29 mL, 1.95 mmol), diethylamine (0.24 mL, 2.35 mmol) and TEA (0.32 mL, 2.35 mmol). The mixture was stirred at room temperature for 12 h and then diluted with EtOAc (50 mL). The reaction mixture was washed with sat. NaHCO3 (50 mL), H2O (50 mL) and brine (50 mL). The organic phase was concentrated to dryness. The crude material was purified by chromatography (silica gel 60 mesh, eluting with 50% hexanes/50% EtOAc) yielding 0.60 g (79%) pure product.

Workup

  1. washThe reaction mixture was washed with sat. NaHCO3 (50 mL), H2O (50 mL) and brine (50 mL)
  2. concentrationThe organic phase was concentrated to dryness
  3. customThe crude material was purified by chromatography (silica gel 60 mesh, eluting with 50% hexanes/50% EtOAc)

Sources & evidence

ORD record
ord-ca400d68c67a44dbbaf6e27d2c4cf0be
Source dataset
uspto-grants-2007_01
Patent number
US07169777B2

Reaction notes

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