Bromotrimethylsilane → HCID 67786124, compound

HRID 1612778Notes

Reaction equation

HRID 1612778 reaction equation
C(OC([NH:8][CH2:9][C:10](=[O:21])[CH2:11][P:12]([CH2:17][CH:18]1[CH2:20][CH2:19]1)(=[O:16])[O:13]CC)=O)(C)(C)C.C[Si](C)(C)[Br:24]>ClCCl.CO>[BrH:24].[NH2:8][CH2:9][C:10](=[O:21])[CH2:11][P:12]([CH2:17][CH:18]1[CH2:20][CH2:19]1)(=[O:13])[OH:16]

Participants

5

Reactant 2

HCID 76113BromotrimethylsilaneHCID 10087300HCID 10087300, compound

Product 1

HCID 67786124HCID 67786124, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 0.64 g of ethyl 3-(N-tert.-butoxycarbonylamino)-2-oxo-propyl(cyclopropylmethyl)phosphinate in 10 ml of anhydrous dichloromethane under an inert atmosphere at room temperature is treated with 1.53 g of trimethylbromosilane. The pale yellow solution is stirred for 4 hours at room temperature and the volatile materials are removed under reduced pressure to give a pale yellow oil. This oil is redissolved in methanol containing 1% water and the clear pale yellow solution is stirred for 30 minutes at room temperature. The solvent is removed and the residue is dried in high vacuum at 50° C. for 24 hours to afford 3-amino-2-oxopropyl(cyclopropylmethyl)phosphinic acid hydrobromide salt as a yellow gum. This gum is dissolved in ethanol and treated with propylene oxide to afford, after filtration and drying 3-amino-2-oxo-propyl(cyclopropylmethyl)phosphinic acid as a pale yellow solid of m.p. 109°-110° C.; 1H-NMR (D2O): δ (ppm)=4.15 (2H, s, CH2N), 3.18 (2H, d, J=15 Hz, CH2P), 1.58 (2H, d, d, J=15+6 Hz, PCH2), 0.83 (1H, m, CH), 0.55 (2H, m, CH2), 0.17 (2H, m, CH2).

Workup

  1. customthe volatile materials are removed under reduced pressure
  2. customto give a pale yellow oil
  3. stirringthe clear pale yellow solution is stirred for 30 minutes at room temperature
  4. customThe solvent is removed
  5. customthe residue is dried in high vacuum at 50° C. for 24 hours

Sources & evidence

ORD record
ord-4e24100458a04ee7a37127c76df6c579
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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