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Sodium Azide → (3R,4S,5R)-3-Azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

HRID 1773017
Notes
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Reaction equation

HRID 1773017 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@H:9]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[C@H:8](OS(C)(=O)=O)[CH:7]=1)=[O:5])[CH3:2].[N-:27]=[N+:28]=[N-:29].[Na+]>CS(C)=O.CCOC(C)=O.C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[CH2:11][C@@H:10]([O:12][S:13]([CH3:16])(=[O:15])=[O:14])[C@@H:9]([O:17][S:18]([CH3:21])(=[O:20])=[O:19])[C@H:8]([N:27]=[N+:28]=[N-:29])[CH:7]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 42643351(3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Product 1

HCID 86628951(3R,4S,5R)-3-Azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 1140
Toluene
Solvent
HCID 8857Ethyl AcetateSolvent

Procedure

(3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester 43, product of the preceding experiment) was dissolved in DMSO. To the clear light yellow solution NaN3 was added at room temperature and the suspension was stirred for 3 hours. The orange solution was diluted with EtOAc and toluene and extracted 3 times with aqueous NaHCO3. The organic phase was separated, dried over Na2SO4, filtered and the combined filtrates evaporated in a rotary evaporator at 20° C./70-10 mbar. The remaining yellow oil was dissolved twice in toluene and evaporated in a rotary evaporator at 20° C./70-10 mbar to obtain the crude dry product (3R,4S,5R)-3-azido-4,5-bis-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester (44), as yellow oil which was used in purification. A sample of 4 was obtained from crude 44 via a silica column chromatography using a 1:2 mixture of EtOAc and n-hexane. The combined fractions were evaporated and dried on a rotary evaporator to obtain 44 as a pale yellow oil.

Workup

  1. extractionextracted 3 times with aqueous NaHCO3
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customthe combined filtrates evaporated in a rotary evaporator at 20° C./70-10 mbar
  6. dissolutionThe remaining yellow oil was dissolved twice in toluene
  7. customevaporated in a rotary evaporator at 20° C./70-10 mbar

Sources & evidence

ORD record
ord-165694da6fb94f0f9c440adcf4c46b21
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09250238B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes