Acetone → HCID 53718121, compound

HRID 484410Notes

Reaction equation

HRID 484410 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:11]2[N:10]3[C:14](=[O:22])[O:15][C@H:16]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[C@H:9]3[CH2:8][C:7]=2[CH:6]=1)=[O:4].[N-:23]=[N+:24]=[N-:25].[Na+].CC(C)=O>O1CCCC1.C(Cl)Cl.CO.CO.C(OCC)(=O)C>[N:23]([CH2:2][C:3]([C:5]1[CH:13]=[CH:12][C:11]2[N:10]3[C:14](=[O:22])[O:15][C@H:16]([CH2:17][NH:18][C:19](=[O:21])[CH3:20])[C@H:9]3[CH2:8][C:7]=2[CH:6]=1)=[O:4])=[N+:24]=[N-:25]

Participants

7

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 53863851HCID 53863851, compound

Product 1

HCID 53718121HCID 53718121, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of (+/-)-(1S,9aS),(1R,9aR) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 46, 43 mg) and sodium azide (82 mg) are stirred in aqueous tetrahydrofuran (66%) for 3 days. Acetone (1 ml) is added and the mixture was heated in an oil bath (38°-50°) for 8 hours then concentrated to an aqueous layer and extracted with ethylacetate (6×2 ml). The combined organic layers are dried over magnesium sulfate and concentrated to provide the product as as an oil. The oil is taken up in methylene chloride/methanol and then placed on a 1000μ silica preprative plate and developed in methanol/ethylacetate (10/90, 2×) to give the title compound as an oil, NMR (CDCl3, 300 MHz) 7.79, 7.43, 6.45, 4.63, 4.53, 3.75, 3.38, 3.14 and 2.08 δ; IR (CHCl3) 2100, 1760, 1670 and 1360 cm-1.

Workup

  1. temperaturethe mixture was heated in an oil bath (38°-50°) for 8 hours
  2. concentrationthen concentrated to an aqueous layer
  3. extractionextracted with ethylacetate (6×2 ml)
  4. dry with materialThe combined organic layers are dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto provide the product as as an oil

Sources & evidence

ORD record
ord-0791ced5d30f422594dfd134bb198a38
Source dataset
uspto-grants-1993_07
Patent number
US05231188

Reaction notes

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