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

HRID 1702934Notes

Reaction equation

HRID 1702934 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, compound

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-03b3989dc6f44f01a55c74efa509d1a0
Source dataset
uspto-grants-1982_09
Patent number
US04350637

Reaction notes

Loading…