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

HRID 1934575Notes

Reaction equation

HRID 1934575 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].[Cl-].C(N(CC)CC)C.Cl[S:28]([C:31]1[CH:43]=[CH:42][C:34]2[O:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:33]=2[CH:32]=1)(=[O:30])=[O:29]>>[CH:32]1[C:33]2[C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=3[O:35][C:34]=2[CH:42]=[CH:43][C:31]=1[S:28]([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:30])=[O:29]

Participants

5

Reactant 4

HCID 312ChlorideHCID 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%

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

Sources & evidence

ORD record
ord-d13b6b8bebdc47ed9c97b453232dee84
Source dataset
uspto-grants-2002_05
Patent number
US06384075B1

Reaction notes

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