Dichloromethane → HCID 14103105, compound

HRID 1156798Notes

Reaction equation

HRID 1156798 reaction equation
C([O:3][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([O:30][CH3:31])=[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.ClCCl.Br[Si](C)(C)C.C(OCC)(=O)C>CCOCC.O>[OH:5][P:4]([CH2:16][C:17]([N:19]1[C@H:27]([C:28]([O:30][CH3:31])=[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:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:3]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 76113BromotrimethylsilaneHCID 86738445HCID 86738445, compound

Product 1

HCID 14103105HCID 14103105, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

(S)-7-[[Ethoxy(4-phenylbutyl)-phosphinyl]acetyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid, methyl ester (3.44 g) and dry dichloromethane (15 ml) are added to a flask under an argon atmosphere. Using a gas-tight syringe, bromotrimethylsilane (1.5 ml) is added to the flask, which is stirred for about 16 hours at room temperature. Ethyl acetate (50 ml) and water (10 ml) are added to the flask and stirred for 30 minutes. The mixture is diluted with ether and transferred to a separatory funnel. The organic layer is extracted with saturated sodium bicarbonate (two 25 ml portions) and the extract is acidified to pH 1.0 to precipitate product which is extracted into ethyl acetate. The ethyl acetate extract is washed with brine, run through sodium sulfate to dry, and the solvent is stripped leaving the title compound as an oil (2.99 g).

Workup

  1. stirringstirred for 30 minutes
  2. customtransferred to a separatory funnel
  3. extractionThe organic layer is extracted with saturated sodium bicarbonate (two 25 ml portions)
  4. customto precipitate product which
  5. extractionis extracted into ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washis washed with brine
  8. customto dry

Sources & evidence

ORD record
ord-43e27d6fbb874e57b4e1c541559d8701
Source dataset
uspto-grants-1982_06
Patent number
US04337201

Reaction notes

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