Sodium Azide → HCID 57241986, compound

HRID 1941565Notes

Reaction equation

HRID 1941565 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)=[O:33])(=O)=O.[N-:44]=[N+:45]=[N-:46].[Na+]>CN(C)C=O.O>[CH3:43][O:42][C:39]1[CH:38]=[CH:37][C:36]([CH2:35][O:34][C:32]([N:8]2[CH2:9][C@@H:10]([S:12][C:13]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:11][C@H:7]2[CH2:6][N:44]=[N+:45]=[N-:46])=[O:33])=[CH:41][CH:40]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 10746404HCID 10746404, compound

Product 1

HCID 57241986HCID 57241986, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol methanesulfonate (27.81 g ) in dimethylformamide (120 ml), a solution (12 ml) of sodium azide (3.50 g: 53.8 mmole) in water is added. The mixture is stirred at 80° C. for 8 hours. The reaction mixture is poured into ice water and extracted with ethyl acetate. The extract is successively washed with water and brine and concentrated. The residue is purified by silica gel column chromatography to give (2S, 4S)-1-p-methoxybenzyloxycarbonyl-2-azidomethyl-4-tritylthiopyrrolidine (17.27 g: 30.64 mmole). Total yield of Steps 4 and 5:74%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract is successively washed with water and brine
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-64fb43fada794094b0f4cc6c5cf17f37
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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