Ethyl dichlorophosphate → HCID 178453599, compound

HRID 1483849Notes

Reaction equation

HRID 1483849 reaction equation
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](=O)[NH2:16])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1.P(Cl)(Cl)(OCC)=O.[NH4+].[Cl-]>C(Cl)Cl.CO>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([C:15]#[N:16])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 15158Ethyl dichlorophosphateHCID 25517Ammonium ChlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 178453604HCID 178453604, compound

Product 1

HCID 178453599HCID 178453599, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl((trans-4-carbamoylcyclohexyl)methyl)carbamate (1.7 g, 6.6 mmol) in CH2Cl2 (33 mL) was added DBU (3 g, 19.8 mmol) at room temperature. After stirring for 10 min, ethyl dichlorophosphate (2.2 g, 13.2 mmol) was added. The mixture was stirred at room temperature for 50 min. TLC (CH2Cl2:MeOH=10:1) showed the reaction was complete. The mixture was poured into sat. NH4Cl (aq., 150 mL) and extracted with CH2Cl2 (100 mL*2). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by combi flash to give tert-butyl((trans-4-cyanocyclohexyl)methyl)carbamate (1.4 g, 88%) as a white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 50 min
  2. extractionextracted with CH2Cl2 (100 mL*2)
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by combi flash

Sources & evidence

ORD record
ord-d1aca9b41c6b450295cb3f2291d61ff6
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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