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Acetone → (1S,9aS) N-[(7-Azidoacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo [3,4-a]indol-1-yl)methyl]acetamide

HRID 6237
Notes
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Reaction equation

HRID 6237 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 180AcetoneHCID 33557Sodium AzideHCID 18653087(1S,9aS) N-[(7-Chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide

Product 1

HCID 86747041(1S,9aS) N-[(7-Azidoacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo [3,4-a]indol-1-yl)methyl]acetamide

Reagents, catalysts & solvents 3

HCID 8028Tetrahydrofuran
Solvent
HCID 21226129Dichloromethane methanolSolvent
HCID 21584119Ethylacetate methanolSolvent

Procedure

A mixture of (1S,9aS) N-[(7-chloroacetyl-9,9a-dihydro-3-oxo-1H,3H-oxazolo[3,4-a]indol-1-yl)methyl]acetamide (EXAMPLE 48, 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 100 μsilica preprative plate and developed in methanol/ethylacetate (10/90, 2×) to give the title compound. ##STR2##

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-344b5d26f989476db51adec38886cea4
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05247090

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes