Diethyl cyanophosphonate → HCID 86711160, compound

HRID 1055268Notes

Reaction equation

HRID 1055268 reaction equation
[F:1][C:2]1[CH:39]=[CH:38][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]4[C:22](=[O:23])[N:21]5[CH2:24][CH2:25][CH2:26][CH:27]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34](O)=[O:35])[C:20]5=[N:19][C:18]=4[CH3:37])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.[C:40]([O:44][C:45]([N:47]1[CH2:52][CH2:51][NH:50][CH2:49][CH2:48]1)=[O:46])([CH3:43])([CH3:42])[CH3:41].C(N(C(C)C)CC)(C)C.C(P(=O)(OCC)OCC)#N>ClCCl.O>[F:1][C:2]1[CH:39]=[CH:38][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]4[C:22](=[O:23])[N:21]5[CH2:24][CH2:25][CH2:26][CH:27]([O:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:34]([N:50]6[CH2:51][CH2:52][N:47]([C:45]([O:44][C:40]([CH3:43])([CH3:41])[CH3:42])=[O:46])[CH2:48][CH2:49]6)=[O:35])[C:20]5=[N:19][C:18]=4[CH3:37])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 76257Diethyl cyanophosphonateHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 73331074HCID 73331074, compound

Product 1

HCID 86711160HCID 86711160, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 4 (200 mg, 0.37 mmol) in dichloromethane (10 mL), under argon, was treated with N-t-butoxycarbonylpiperazine (89.57 mg, 0.48 mmol) and diisopropylethylamine (77.42 μL 0.44 mmol). To the stirring solution, diethyl cyanophosphonate (72.06 μL, 0.43 mmol) was added. After stirring for two hours at room temperature, the reaction mixture was poured into water (20 mL) and the aqueous layer extracted with dichloromethane (three times 20 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude mixture was used without further purification in the next step. (408 mg, ESI-MS (M+1) 709)

Workup

  1. extractionthe aqueous layer extracted with dichloromethane (three times 20 mL)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude mixture was used without further purification in the next step

Sources & evidence

ORD record
ord-584b4e9d9bc643df98a82178d162f141
Source dataset
uspto-grants-2016_07
Patent number
US09394354B2

Reaction notes

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