Ethyl dichlorophosphate → HCID 89544838, compound

HRID 2283413Notes

Reaction equation

HRID 2283413 reaction equation
[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=O)[NH2:27])[CH:21]=2)[C:12]=1[F:30])[CH2:9][CH3:10])([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(OCC)=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.O>[C:1]([O:5][C:6](=[O:31])[NH:7][C@@H:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([C:19](=[O:29])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]#[N:27])[CH:21]=2)[C:12]=1[F:30])[CH2:9][CH3:10])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 15158Ethyl dichlorophosphateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 89544735HCID 89544735, compound

Product 1

HCID 89544838HCID 89544838, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Step 4 A mixture of {(R)-1-[3-(3-carbamoyl-benzoyl)-2-fluoro-4-methoxy-phenyl]-propyl}-carbamic acid tert-butyl ester (269 mg, 0.62 mmol) from Step 3, ethyl dichlorophosphate (0.14 mL, 1.25 mmol, 2 eq.) and DBU (0.28 mL, 1.87 mmol, 3 eq.) in DCM (3 mL) was stirred for 24 hours. The mixture was then diluted with DCM (15 mL) and water (15 mL) and the organic phase was washed with brine, isolated by phase separation and concentrated to give crude {(R)-1-[3-(3-cyano-benzoyl)-2-fluoro-4-methoxy-phenyl]-propyl}-carbamic acid tert-butyl ester which was used in the next step. [M−H]− 411

Workup

  1. washthe organic phase was washed with brine
  2. customisolated by phase separation
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cf7d0c3b139f4b929afe350641ae2ba4
Source dataset
uspto-grants-2015_09
Patent number
US09145354B2

Reaction notes

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