Hydrochloric Acid → HCID 11362878, compound

HRID 1791028Notes

Reaction equation

HRID 1791028 reaction equation
CN1CCCN(C)C1=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:20]=[C:21]1[CH2:27][CH:26]([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:25]2[CH:37]=[C:38]([C:41]([O:43][CH3:44])=[O:42])[CH:39]=[CH:40][C:24]=2[O:23][CH2:22]1.[CH2:45](Br)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1.Cl>O1CCCC1.ClCCl.O>[CH2:45]([C:26]1([S:28]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:30])=[O:29])[C:25]2[CH:37]=[C:38]([C:41]([O:43][CH3:44])=[O:42])[CH:39]=[CH:40][C:24]=2[O:23][CH2:22][C:21](=[CH2:20])[CH2:27]1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 2733832Lithium HexamethyldisilazideHCID 11439769HCID 11439769, compound

Product 1

HCID 11362878HCID 11362878, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

0.072 ml (1.1 equivalents) of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone and then 0.6 ml (1.1 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 195 mg (0.55 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 1, in solution in 5 ml of tetrahydrofuran. The reaction medium then assumes a dark yellow color. After stirring for 15 minutes, 0.073 ml (1.1 equivalents) of benzyl bromide is added. After stirring for 5 minutes, water, 1N hydrochloric acid and dichloromethane are added. After separating the organic and aqueous phases, the aqueous phase is extracted three times with dichloromethane. The combined organic phases are washed with brine, are dried and are finally concentrated under vacuum. The crude reaction product is then purified by chromatography on silica gel (ethyl acetate/heptane 25/75) to provide 211 mg (86%) of methyl 5-benzyl-3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate in the form of a white solid; M.p.=164–165° C.

Workup

  1. customprepared
  2. stirringAfter stirring for 5 minutes
  3. customAfter separating the organic and aqueous phases
  4. extractionthe aqueous phase is extracted three times with dichloromethane
  5. washThe combined organic phases are washed with brine
  6. customare dried
  7. concentrationare finally concentrated under vacuum
  8. customThe crude reaction product
  9. customis then purified by chromatography on silica gel (ethyl acetate/heptane 25/75)

Sources & evidence

ORD record
ord-8e1a81dcc4f34c74882563a072dc0774
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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