Bromotrimethylsilane → HCID 13118412, compound

HRID 1649347Notes

Reaction equation

HRID 1649347 reaction equation
C([O:3][P:4]([CH2:24][C:25]([N:27]1[CH2:41][CH2:40][CH2:39][C@H:28]1[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:30])=[O:26])([CH:6]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])C.Br[Si](C)(C)C>ClCCl>[OH:5][P:4]([CH2:24][C:25]([N:27]1[CH2:41][CH2:40][CH2:39][C@H:28]1[C:29]([O:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)=[O:30])=[O:26])([CH:6]([CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:7][C:8](=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)=[O:3]

Participants

4

Reactant 2

HCID 76113Bromotrimethylsilane2×HCID 13118410HCID 13118410, compound

Product 1

HCID 13118412HCID 13118412, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product from part (e) (1.146 g., 1.99 mmole) in dry dichloromethane (6 ml.) is treated with bromotrimethylsilane (0.55 ml., 4.17 mmole) and stirred at room temperature under argon. After 3 hours, additional bromotrimethylsilane (0.2 ml.) is added and stirring continued for 1 hour. The excess bromotrimethylsilane and dichloromethane are removed in vacuo and the residue is treated with water and ethyl acetate and stirred for 15 minutes. The aqueous phase is separated and the ethyl acetate layer is washed with saturated sodium chloride, dried over Na2SO4 and evaporated to give (±)-1-[[hydroxy[3-oxo-3-phenyl-1-(2-phenylethyl)propyl]phosphinyl]acetyl]-L-proline, phenylmethyl ester (100%) as a white foam, Rf (acetic acid/methanol/dichloromethane 1:1:18) 0.42.

Workup

  1. stirringstirring
  2. waitcontinued for 1 hour
  3. customThe excess bromotrimethylsilane and dichloromethane are removed in vacuo
  4. additionthe residue is treated with water and ethyl acetate
  5. stirringstirred for 15 minutes
  6. customThe aqueous phase is separated
  7. washthe ethyl acetate layer is washed with saturated sodium chloride
  8. dry with materialdried over Na2SO4
  9. customevaporated

Sources & evidence

ORD record
ord-2ff52db565c0446696976dc9979eb330
Source dataset
uspto-grants-1983_11
Patent number
US04416833

Reaction notes

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