4,7-Methanoisobenzofuran-1(3H)-one, 3a,4,7,7a-tetrahydro-3-hydroxy- → HCID 57283447, compound

HRID 1981239Notes

Reaction equation

HRID 1981239 reaction equation
[NH2:1][C@H:2]([C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[OH:17][CH:18]1[CH:26]2[CH:21]([CH:22]3[CH2:27][CH:25]2[CH:24]=[CH:23]3)[C:20](=O)[O:19]1>C1C=CC=CC=1>[O:17]=[C:18]1[C@H:26]2[C@H:21]([C@@H:22]3[CH2:27][C@H:25]2[CH:24]=[CH:23]3)[C@@H:20]([NH:1][C@@H:2]([CH2:3][CH:4]([CH3:6])[CH3:5])[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[O:19]1

Participants

4

Reactant 2

HCID 5487574,7-Methanoisobenzofuran-1(3H)-one, 3a,4,7,7a-tetrahydro-3-hydroxy-HCID 6451313Benzyl L-leucinate

Product 1

HCID 57283447HCID 57283447, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.2 g of benzyl L-leucinate, 4 g of (3RS,3aRS,4RS,7RS,7aRS)3-hydroxy-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran-1-one and 40 ml of anhydrous benzene was refluxed for 90 minutes while azeotropically distilling off the water of reaction formed and was then evaporated to dryness under reduced pressure. The residue was added to isopropyl ether and the mixture was vacuum filtered to obtain 2.3 g of benzyl (αS,3S,3aS,4R,7S,7aR)α-[(1-oxo-3a,4,7,7a-tetrahydro-1H,3H-4,7-methano-isobenzofuran-3-yl)-amino]-isohexanoate melting at 95° C.

Workup

  1. temperaturewas refluxed for 90 minutes
  2. distillationwhile azeotropically distilling off
  3. customthe water of reaction
  4. customformed
  5. customwas then evaporated to dryness under reduced pressure
  6. additionThe residue was added to isopropyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-9bddea025a094580be6ce32d5596efe6
Source dataset
uspto-grants-1985_04
Patent number
US04513139

Reaction notes

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