Bromotrimethylsilane → HCID 67785200, compound

HRID 1612769Notes

Reaction equation

HRID 1612769 reaction equation
C([CH:3]([NH:17]C(OC(C)(C)C)=O)[C:4](=[O:16])[CH2:5][P:6]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(=[O:8])[O-:7])C.C[Si](C)(C)[Br:27]>ClCCl.CO.O>[BrH:27].[NH2:17][CH2:3][C:4](=[O:16])[CH2:5][P:6]([CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1)(=[O:7])[OH:8]

Participants

6

Reactant 2

HCID 76113BromotrimethylsilaneHCID 86746589HCID 86746589, compound

Product 1

HCID 67785200HCID 67785200, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1.0 g of ethyl-3-(N-tert.-butoxycarbonylamino)-2-oxopropyl(cyclohexylmethyl)phosphinate in 15 ml of anhydrous dichloromethane under an inert atmosphere at room temperature is treated with 2.1 g of trimethylbromosilane. After stirring for 7 hours the volatile components are removed under reduced pressure to give a pale yellow oil. This oil is dissolved in methanol containing 1% of water and the clear pale yellow solution is stirred overnight at room temperature. The solvent is removed under reduced pressure to afford 3-amino-2-oxo-propyl(cyclohexylmethyl)phosphinic acid hydrobromide, m.p. 180°-182° C. Suspension in ethanol and treatment with propylene oxide affords 3-amino-2-oxo-propyl(cyclohexylmethyl)phosphinic acid, 1H-NMR (D2O): δ (ppm)=4.15 (2H, s, CH2N), 3.10 (2H, d, J=15 Hz, CH2 --P), 1.80 (2H, m, P--CH2), 1.73-1.52 (5H, m, 2×CH2 +CH), 1.34-0.95 (6H, m, 3×CH2).

Workup

  1. customare removed under reduced pressure
  2. customto give a pale yellow oil
  3. stirringthe clear pale yellow solution is stirred overnight at room temperature
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e442fba688c6429ab19ebd30abf54e55
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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