Bromotrimethylsilane → HCID 57289203, compound

HRID 1156805Notes

Reaction equation

HRID 1156805 reaction equation
C([O:3][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([O:30][CH2:31][O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])=[O:29])[CH2:26][C:21]2([S:25][CH2:24][CH2:23][S:22]2)[CH2:20]1)=[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[C@H:27]([C:28]([O:30][CH2:31][O:32][C:33](=[O:38])[C:34]([CH3:36])([CH3:35])[CH3:37])=[O:29])[CH2:26][C:21]2([S:22][CH2:23][CH2:24][S:25]2)[CH2:20]1)=[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:3]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 57123529HCID 57123529, compound

Product 1

HCID 57289203HCID 57289203, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-7-[[Ethoxy(4-phenylbutyl)phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, (2,2-dimethyl-1-oxopropoxy)methyl ester (2.7 g) in dichloromethane (dried over alumina) is treated with bromotrimethylsilane (1.2 ml) via syringe and the reaction mixture is stirred for 16 hours under argon. The solvent and excess bromotrimethylsilane is evaporated in vacuo and the residue is taken up in ethyl acetate and water and stirred for 15 minutes. The layers are separated and the ethyl acetate is washed with 5% potassium sulfate, water, brine dried (MgSO4) and evaporated. The 2.3 g of crude product is chromatographed on silica (75 g) eluting with dichloromethane/methanol/acetic acid (19/0.5/0.5). After stripping solvent 1.9 g of product is left as a glass.

Workup

  1. customThe solvent and excess bromotrimethylsilane is evaporated in vacuo
  2. stirringwater and stirred for 15 minutes
  3. customThe layers are separated
  4. washthe ethyl acetate is washed with 5% potassium sulfate, water, brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe 2.3 g of crude product is chromatographed on silica (75 g)
  8. washeluting with dichloromethane/methanol/acetic acid (19/0.5/0.5)
  9. waitis left as a glass

Sources & evidence

ORD record
ord-7f72166eca3d40fe8071a3e125ac1311
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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