Triethylamine → methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate

HRID 565616Notes

Reaction equation

HRID 565616 reaction equation
[NH2:1][C@@H:2]1[C@H:7]2[CH2:8][C@H:4]([CH2:5][CH2:6]2)[C@H:3]1[CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16].C(N(CC)CC)C.Cl[S:27]([C:30]1[CH:42]=[CH:41][C:33]2[O:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[C:32]=2[CH:31]=1)(=[O:29])=[O:28]>C(Cl)Cl>[CH:31]1[C:32]2[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=3[O:34][C:33]=2[CH:41]=[CH:42][C:30]=1[S:27]([NH:1][C@@H:2]1[C@H:7]2[CH2:8][C@H:4]([CH2:5][CH2:6]2)[C@H:3]1[CH2:9]/[CH:10]=[CH:11]\[CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27580308-Oxatricyclo(7.4.0.0,2,7)trideca-1(9),2(7),3,5,10,12-hexaene-4-sulfonyl chlorideHCID 14134676HCID 14134676, compound

Product 1

HCID 131722261methyl (Z)-7-[(1S,2R,3R,4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (Z)-7-[(1S,2R,3R,4R)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (II-1) (251 mg, 1.00 mmol) was dissolved in methylene chloride (8 ml) and triethylamine (0.238 ml, 2.00 mmol) was added thereto under a nitrogen atmosphere. To the mixture was added 2-chlorosulfonyldibenzofuran (350 mg, 1.31 mmol) under ice-cooling, and the mixture was stirred for 30 min and allowed to warm up to room temperature. The reaction mixture was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:4)) and recrystallized from n-hexane (10 ml) to yield methyl (Z)-7-[(1S, 2R, 3R, 4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1a-1) (342 mg, 0.710 mmol). Yield 71%, mp 115-116° C.

Workup

  1. temperaturecooling
  2. customThe reaction mixture was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:4))
  3. customrecrystallized from n-hexane (10 ml)

Sources & evidence

ORD record
ord-7781c846b4c3472da1590bf21b840671
Source dataset
uspto-grants-2001_01
Patent number
US06172113B2

Reaction notes

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