Bromotrimethylsilane → HCID 12962079, compound

HRID 1156810Notes

Reaction equation

HRID 1156810 reaction equation
C([O:3][P:4]([CH2:16][C:17]([N:19]1[CH2:34][C@@H:33]([O:35][CH3:36])[CH2:32][C@H:20]1[C:21]([O:23][CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:22])=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:5])C.Br[Si](C)(C)C>ClCCl>[OH:5][P:4]([CH2:16][C:17]([N:19]1[CH2:34][C@@H:33]([O:35][CH3:36])[CH2:32][C@H:20]1[C:21]([O:23][CH2:24][O:25][C:26](=[O:31])[C:27]([CH3:28])([CH3:29])[CH3:30])=[O:22])=[O:18])([CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 22823216HCID 22823216, compound

Product 1

HCID 12962079HCID 12962079, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.9 g of (cis)-1-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-4-methoxy-L-proline, (2,2-dimethyl-1-oxopropoxy)methyl ester in 50 ml of dry dichloromethane is treated with 1.0 g of bromotrimethylsilane at 0° C., then stirred at room temperature for 16 hours under argon. The solvent is evaporated in vacuo and the oil residue is dissolved in ether and treated with an excess of saturated sodium. The aqueous portion is treated with 6 N HCl to pH 1.5 and the product is extracted into ethyl acetate, dried and evaporated in vacuo to give 1.4 g of product.

Workup

  1. customThe solvent is evaporated in vacuo
  2. dissolutionthe oil residue is dissolved in ether
  3. additiontreated with an excess of saturated sodium
  4. additionThe aqueous portion is treated with 6 N HCl to pH 1.5
  5. extractionthe product is extracted into ethyl acetate
  6. customdried
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ec8d07e25644414cb370340b7db0c147
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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