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Hydrochloric Acid → HCID 11451992, compound

HRID 1791031
Notes
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Reaction equation

HRID 1791031 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH2:11]=[C:12]1[CH2:18][CH:17]([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:16]2[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=[CH:31][C:15]=2[O:14][CH2:13]1.[CH2:36](Br)[CH3:37].Cl>O1CCCC1.ClCCl.O>[CH2:36]([C:17]1([S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:16]2[CH:28]=[C:29]([C:32]([O:34][CH3:35])=[O:33])[CH:30]=[CH:31][C:15]=2[O:14][CH2:13][C:12](=[CH2:11])[CH2:18]1)[CH3:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6332Ethyl BromideHCID 2733832Lithium hexamethyldisilazaneHCID 11439769HCID 11439769, compound

Product 1

HCID 11451992HCID 11451992, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 962
Water
Solvent
HCID 6344DichloromethaneSolvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

0.030 ml (1.1 equivalents) of 1,3-dimethylpropyleneurea and then 0.246 ml (1.1 equivalents) of 1.06M lithium bis(trimethylsilyl)amide in tetrahydrofuran are added at ambient temperature to 80 mg (0.22 mmol) of methyl 3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate, prepared according to example 1, in solution in 2.2 ml of tetrahydrofuran. The reaction medium then assumes a dark yellow color. After stirring for 15 minutes, 0.0185 ml (1.1 equivalents) of ethyl 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 give 56 mg (58%) of methyl 5-ethyl-3-methylene-5-(phenylsulfonyl)-2,3,4,5-tetrahydro-1-benzoxepin-7-carboxylate in the form of an oil; 1H NMR (300 MHz, CDCl3): 0.97 (t, J=7.3 Hz, 3H), 2.41 (q, J=7.3 Hz, 2H), 3.83 (s, 3H), 4.28 (d, J=14.7 Hz, 1H), 4.58 (d, J=14.7 Hz, 1H), 4.86 (s, 1H), 5.02 (s, 1H), 6.82 (d, J=8.5 Hz, 1H), 7.35 (m, 5H), 7.85 (dd, J=8.46 and 2 Hz, 1H), 8.08 (d, J=2.07 Hz, 1H).

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-c49d4299a4bd4422926a75399ae58a44
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07071340B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes