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Sodium Iodide → N-[5-((R)-2-azido-1-hydroxyethyl)-2-benzyloxyphenyl]methanesulfonamide

HRID 1370199
Notes
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Reaction equation

HRID 1370199 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:18])[CH2:16]Br)=[CH:11][C:10]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[Na+].[N-:26]=[N+:27]=[N-:28].[Na+]>CS(C)=O>[N:26]([CH2:16][C@@H:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[C:10]([NH:19][S:20]([CH3:23])(=[O:22])=[O:21])[CH:11]=1)[OH:18])=[N+:27]=[N-:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 33557Sodium AzideHCID 22220535n-[2-Benzyloxy-5-(2-bromo-1-hydroxy-ethyl)-phenyl]-methanesulfonamide

Product 1

HCID 86611776N-[5-((R)-2-azido-1-hydroxyethyl)-2-benzyloxyphenyl]methanesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 679Dimethyl Sulfoxide
Solvent

Procedure

To a stirred solution of N-[2-benzyloxy-5-(2-bromo-1-hydroxy-ethyl)-phenyl]-methanesulfonamide (Washburn, W. N., et al., EP 0 659 737) (15.05 g, 38 mmol) in dimethyl sulfoxide (150 ml) was added sodium iodide (3.76 g, 376 mmol) and sodium azide (9.48 g, 150 mmol). The mixture was stirred for 5 days under nitrogen atmosphere. The reaction mixture was poured onto water and extracted three times with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated. The residue was triturated with water and hexanes to give the title compound as a yellow solid (12.85 g, 94%): 1H NMR (300 MHz, CDCl3) δ 2.93(s, 3 H), 3.47(d, J=5.4 Hz, 2 H), 4.84(t, J=5.4 Hz, 1 H), 5.11(s, 2 H), 6.80(s, 1 H), 6.99(d, J=8.4 Hz, 1 H), 7.15(dd, J=8.4 Hz, 2.1 Hz, 1 H), 7.26(s, 1 H), 7.30-7.50(m, 5H), 7.53(d, J=2.1 Hz, 1 H); MS (ES) m/z 361.4 ((M−H)−, 70%).

Workup

  1. additionThe reaction mixture was poured onto water
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was triturated with water and hexanes

Sources & evidence

ORD record
ord-dd6f9988b0ed442482c85322c2b0350e
Source dataset
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06583140B2

Reaction notes

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