Methyl N-(triethylammoniosulfonyl)carbamate → HCID 68699248, compound

HRID 1172900Notes

Reaction equation

HRID 1172900 reaction equation
FC(C1OC(C2C=CC=CC=2)=NN=1)C1C=CC2C=C(C(O)=O)SC=2C=1.[C:26]([NH:34][NH:35][C:36](=[O:53])[CH:37]([C:39]1[CH:52]=[CH:51][C:42]2[CH:43]=[C:44]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[S:45][C:41]=2[CH:40]=1)[F:38])(=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C1COCC1>[F:38][CH:37]([C:36]1[O:53][C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[N:34][N:35]=1)[C:39]1[CH:52]=[CH:51][C:42]2[CH:43]=[C:44]([C:46]([O:48][CH2:49][CH3:50])=[O:47])[S:45][C:41]=2[CH:40]=1

Participants

5

Reactant 3

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 59556410HCID 59556410, compoundHCID 68693560HCID 68693560, compound

Product 1

HCID 68699248HCID 68699248, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

Dehydration/Saponification; 6-[Fluoro-(5-phenyl-[1,3,4]oxadiazol-2-yl)-methyl]-benzo[b]thiophene-2-carboxylic acid. A solution of ethyl 6-[2-(2-benzoylhydrazino)-1-fluoro-2-oxoethyl]-1-benzothiophene-2-carboxylate (51 mg, 0.13 mmol) in THF (2.0 mL) was treated with Burgess reagent (45 mg, 0.19 mmol). The reaction vessel was sealed and heated to 120° C. in the microwave reactor for 20 minutes. The reaction was evaporated in vacuo and purified by flash chromatography (10-40% ethyl acetate/hexanes) to give ethyl 6-[fluoro(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1-benzothiophene-2-carboxylate as a white solid. ESIMS calcd 383.1 (M++H), found 383.0 (M++H). To a solution of ethyl 6-[fluoro(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1-benzothiophene-2-carboxylate in THF (2.5 mL) was added 1M sodium hydroxide (5.0 mL, 5.0 mmol) and the resulting solution was stirred at ambient temperature for 1 hour. The reaction was partitioned between ethyl acetate and 1M HCl solution. The organics were dried over sodium sulfate, filtered and evaporated to give 6-[fluoro(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1-benzothiophene-2-carboxylic acid as a white solid. ESIMS calcd 355.1 (M++H), found 355.0 (M++H).

Workup

  1. customThe reaction vessel was sealed
  2. customThe reaction was evaporated in vacuo
  3. custompurified by flash chromatography (10-40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-86dda7ffbe2040b78b42e26ef71c108f
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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