Phosphorus sulfide (P2S5) → HCID 86722618, compound

HRID 587769Notes

Reaction equation

HRID 587769 reaction equation
O=[C:2]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].C[Si](C)(C)O[Si](C)(C)C>C(Cl)Cl>[S:20]=[C:2]([NH:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C@H:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:4]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)2×HCID 24764HexamethyldisiloxaneHCID 86676717HCID 86676717, compound

Product 1

HCID 86722618HCID 86722618, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (R)-tert-butyl 1-oxo-1-(2,2,2-trifluoroethylamino)propan-2-ylcarbamate (100 mg, 0.37 mmol) in CH2Cl2 (10 mL) was added P2S5 (24 mg, 0.11 mmol) and hexamethyldisiloxane (HMDO) (0.13 mL, 0.59 mmol) at room temperature and the mixture was refluxed for 3 h. The reaction mixture was cooled to room temperature and another portion of P2S5 (24 mg, 0.11 mmol) was added and the resulting mixture was refluxed for 18 h. The volatiles were evaporated, pentane (25 mL) was added to the residue and stirred for 10-15 min. The pentane layer was decanted, concentrated in vacuo and the residue was passed through a short silica pad eluting with pentane followed by CH2Cl2 to give the title compound as colorless liquid (30 mg, 30%): 1H NMR (400 MHz, DMSO-d6) δ 10.27 (t, J=5.4 Hz, 1H), 7.00 (d, J=6.8 Hz, 1H), 4.57-4.35 (m, 3H), 1.32 (s, 9H), 1.25 (d, J=7.6 Hz, 3H); ESIMS m/z 286.2 ([M+H]+); IR (thin film) 3233, 1683, 1257 cm−1.

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. temperaturethe resulting mixture was refluxed for 18 h
  3. customThe volatiles were evaporated
  4. additionpentane (25 mL) was added to the residue
  5. customThe pentane layer was decanted
  6. concentrationconcentrated in vacuo
  7. washeluting with pentane

Sources & evidence

ORD record
ord-a9c942efd6a1424c967981afc23dc01c
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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