HCID 86751484, compound → HCID 86751483, compound

HRID 2292448Notes

Reaction equation

HRID 2292448 reaction equation
[C:1]([N:4]1[C:22](=[O:23])[NH:21][C:20](=[O:24])[C@@:5]21[O:9][C@@H:8]([CH2:10]I)[C@H:7]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]2[O:16][C:17](=[O:19])[CH3:18])(=[O:3])[CH3:2].[C:25]([O-:28])(=[S:27])[CH3:26].C[N+](C)(C)C>COCCOC.ClCCl>[C:1]([N:4]1[C:22](=[O:23])[NH:21][C:20](=[O:24])[C@@:5]21[O:9][C@@H:8]([CH2:10][S:27][C:25](=[O:28])[CH3:26])[C@H:7]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]2[O:16][C:17](=[O:19])[CH3:18])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 86751484HCID 86751484, compoundHCID 178477156HCID 178477156, compound

Product 1

HCID 86751483HCID 86751483, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
45 °C

Procedure

To a solution of (2R, 3R, 4R, 5S)-6-acetyl-2-iodomethyl-3, 4-diacetoxy-1-oxa-6,8-diazaspiro (4,4) nonane-7, 9-dione (598 mg, 1.32 mm) in anhydrous DME (10 ml) is added, under N2, tetramethylammonium thioacetate (353 mg, 2.37 mm) in one portion. The resulting mixture is heated at 45° C. for 4 hours, then diluted with dichloromethane and washed with brine, dried, and evaporated for dryness. The crude product is purified by thin-layer chromatography to give (2R, 3R, 4R, 5S)-6-acetyl-2-acetylthiomethyl-3, 4-diacetoxy-1-oxa-6, 8-diazaspiro (4,4) nonane-7, 9-dione (500 mg) as a hygroscopic foam.

Workup

  1. washwashed with brine
  2. customdried
  3. customevaporated for dryness
  4. customThe crude product is purified by thin-layer chromatography

Sources & evidence

ORD record
ord-7691e927f5ea4806b74f561950427f79
Source dataset
uspto-grants-1997_11
Patent number
US05683963

Reaction notes

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