Hydrochloric Acid → HCID 19366862, compound

HRID 849542Notes

Reaction equation

HRID 849542 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:21][CH:22]([NH:35][C:36](=[O:38])[CH3:37])[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25].C(OC([N+](C(OCC)=O)=[N-])=O)C.C(O)(=[S:53])C.C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(CC(NC(=O)C)CS(C1C=CC(OC)=CC=1)(=O)=O)(=S)C.C[O-].[Na+].Cl>O1CCCC1.CO>[SH:53][CH2:21][CH:22]([NH:35][C:36](=[O:38])[CH3:37])[CH2:23][S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1)(=[O:26])=[O:25]

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 13097Triphenylphosphine OxideHCID 10942334Sodium MethoxideHCID 14357405DiethyldiazodicarboxylateHCID 19366864HCID 19366864, compoundHCID 19366875HCID 19366875, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 19366862HCID 19366862, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Part C: (471 mg, 1.8 mmol) of triphenylphosphine and (520 mg, 1.8 mmol) of N-[1-(hydroxymethyl)-2-[(4-methoxyphenyl)sulfonyl)ethyl)acetamide were dissolved in 15 mL of tetrahydrofuran and cooled to zero C. under nitrogen atmosphere. To this was added (313 mg, 1.8 mmol) of diethyldiazodicarboxylate, followed by (140 mg, 1.8 mmol) of thioacetic acid and the solution stirred for 2 hours. The resulting clear solution was concentrated by rotory evaporation and subjected to silica gel chromatography using 15% methanol in ethyl acetate as the eluant to provide a mixture of triphenylphosphine oxide and the desired N-[1-(thioacetylmethyl)-2-[(4-methoxyphenyl)sulfonyl)ethyl)acetamide in equal molar ratios. This mixture was dissolved in 10 ml of methanol and to this was added 1 mL of 25% sodium methoxide in methanol and this stirred for 30 minutes. The solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate. The resulting organics were concentrated and purified by reverse phase C18 chromatography to yield 150 mg of N-[1-(mercaptomethyl)-2-[(4-methoxyphenyl)sulfonyl)ethyl)acetamide, m/e=310 (M+Li).

Workup

  1. temperaturecooled to zero C
  2. concentrationThe resulting clear solution was concentrated by rotory evaporation
  3. customto provide
  4. stirringthis stirred for 30 minutes
  5. extractionextracted with ethyl acetate
  6. concentrationThe resulting organics were concentrated
  7. custompurified by reverse phase C18 chromatography

Sources & evidence

ORD record
ord-4ef302b1e6084532a0c038723b56c904
Source dataset
uspto-grants-2000_01
Patent number
US06013649

Reaction notes

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