Sodium Azide → HCID 86673836, compound

HRID 1527388Notes

Reaction equation

HRID 1527388 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@:11]([OH:19])([CH2:13]OS(C)(=O)=O)[CH2:10][C@H:9]1[C:20](=[O:31])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[F:30])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N-:32]=[N+:33]=[N-:34].[Na+]>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@:11]([CH2:13][N:32]=[N+:33]=[N-:34])([OH:19])[CH2:10][C@H:9]1[C:20](=[O:31])[NH:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=1[F:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86673835HCID 86673835, compound

Product 1

HCID 86673836HCID 86673836, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (2S,4S)-2-(3-chloro-2-fluoro-benzylcarbamoyl)-4-hydroxy-4-methanesulfonyloxy methyl-pyrrolidine-1-carboxylic acid tert-butyl ester (580 mg, 1.21 mmol) (prepared as described Scheme B13) in DMF (20 mL) was added sodium azide (392 mL, 6.03 mmol) and the solution was stirred for 16 h at 80° C. The reaction mixture was diluted with EtOAc, washed with a saturated aqueous solution of NaHCO3 (3 times). The organic layers were dried (Na2SO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1) to give the desired material. MS (LC/MS): 430.1/432.1 [M+H]+, 374.1 [MH−tBu]+, 332 [MH−Boc]+; tR (HPLC conditions f): 2.22 min.

Workup

  1. washwashed with a saturated aqueous solution of NaHCO3 (3 times)
  2. dry with materialThe organic layers were dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash column chromatography on silica gel (c-hexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-3bd0b418234747a98230755fa9e863c2
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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