Dimethylformamide → (S)-2-amino-2-(3-fluoro-5-iodophenyl)ethyl di-tert-butyl phosphate

HRID 596042Notes

Reaction equation

HRID 596042 reaction equation
[C:1]([O:5][P:6]([O:13][CH2:14][C@@H:15]([NH:24]C(=O)OCC1C2C=CC=CC=2C2C1=CC=CC=2)[C:16]1[CH:21]=[C:20]([I:22])[CH:19]=[C:18]([F:23])[CH:17]=1)([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C=O)C.N1CCCCC1.C(N1CCCCC1)(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O>C(OCC)(=O)C>[P:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])([O:13][CH2:14][C@@H:15]([NH2:24])[C:16]1[CH:21]=[C:20]([I:22])[CH:19]=[C:18]([F:23])[CH:17]=1)=[O:7]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8082PiperidineHCID 21896484(9H-fluoren-9-yl)methyl piperidine-1-carboxylateHCID 118054603(S)-(9H-fluoren-9-yl)methyl (2-((di-tert-butoxyphosphoryl)oxy)-1-(3-fluoro-5-iodophenyl)ethyl)carbamate

Product 1

HCID 118045308(S)-2-amino-2-(3-fluoro-5-iodophenyl)ethyl di-tert-butyl phosphate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To (S)-(9H-fluoren-9-yl)methyl (2-((di-tert-butoxyphosphoryl)oxy)-1-(3-fluoro-5-iodophenyl)ethyl)carbamate (6450 mg, 9.27 mmol) was added DMF (Volume: 90 mL) followed by piperidine (25 mL, 253 mmol) and stirred at room temperature for 30 minutes, followed by LCMS. To the crude reaction mixture was added 750 ml of ethyl acetate, washed with saturated sodium bicarbonate (2×), water (5×), saturated salt solution, dried sodium sulfate, and filtered. The solvent was concentrated off to constant mass under high vacuum to give the desire crude product which includes FMOC piperidine impurity, used as is. LCMS (m/z): 474.2 (MH+), 0.80 min.

Workup

  1. customTo the crude reaction mixture
  2. washwashed with saturated sodium bicarbonate (2×), water (5×), saturated salt solution, dried sodium sulfate
  3. filtrationfiltered
  4. concentrationThe solvent was concentrated off to constant mass under high vacuum
  5. customto give the desire crude product which
  6. custom474.2 (MH+), 0.80 min.

Sources & evidence

ORD record
ord-19e6287ad4b94eaaa8dc70079e006e6c
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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