Methanol → HCID 86601852, compound

HRID 417809Notes

Reaction equation

HRID 417809 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([P:8]([N:27]([CH2:31][CH2:32][Cl:33])[CH2:28][CH2:29][Cl:30])([O:10][CH2:11][CH2:12][S:13][CH2:14][C@@H:15]([C:24]([OH:26])=[O:25])[NH:16]C(OC(C)(C)C)=O)=[O:9])[CH2:5][CH2:6][Cl:7].Cl[Si](C)(C)[CH3:36].CO>ClCCl.C(OCC)(=O)C>[CH3:36][O:26][C:24](=[O:25])[C@H:15]([CH2:14][S:13][CH2:12][CH2:11][O:10][P:8]([N:27]([CH2:31][CH2:32][Cl:33])[CH2:28][CH2:29][Cl:30])([N:4]([CH2:5][CH2:6][Cl:7])[CH2:3][CH2:2][Cl:1])=[O:9])[NH2:16]

Participants

6

Reactant 3

HCID 887MethanolHCID 6397ChlorotrimethylsilaneHCID 86601853HCID 86601853, compound

Product 1

HCID 86601852HCID 86601852, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

3-[[2-[[Bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-N-tert-butoxycarbonyl-L-alanine, 5.0 g (8.4 mmol), prepared as in Synthetic Example 2, was dissolved in 35 mL dichloromethane, and 5.3 mL (42 mmol) chlorotrimethyl silane added with stirring at 0° C., followed by 80 mL methanol. With continued stirring, the mixture was allowed to warm to room temperature, then stirred overnight. The solvents were then removed under vacuum to give a light yellow oil. This was dissolved in ethyl acetate and precipitated with diethyl ether. Filtration and concentration of the filtrate gave two fractions of 3-[[2-[[bis[bis(2-chloroethyl)amino]phosphinyl]oxy]ethyl]thio]-L-alanine methyl ester, totaling 4.87 g. Purity (96%) and identity were verified by ELSD and LC-MS (m/z 508 (M+2+H)+).

Workup

  1. stirringWith continued stirring
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. customThe solvents were then removed under vacuum
  5. customto give a light yellow oil
  6. customprecipitated with diethyl ether
  7. filtrationFiltration and concentration of the filtrate

Sources & evidence

ORD record
ord-69504179da8d4acda9c63367926becc2
Source dataset
uspto-grants-2012_01
Patent number
US08093231B2

Reaction notes

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