Sodium Carbonate → HCID 59085849, compound

HRID 397479Notes

Reaction equation

HRID 397479 reaction equation
CS(O[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][NH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[N:26]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][NH:15][C:16](=[O:17])[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[N+:27]=[N-:28]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 33557Sodium Azide2×HCID 23000604HCID 23000604, compound

Product 1

HCID 59085849HCID 59085849, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.15 g (3.16 mmol) of 2-[2-({[(benzyloxy)carbonyl]amino}methyl)phenyl]ethyl methanesulfonate in 8.0 mL of DMF was added 0.411 g (6.33 mmol) of sodium azide. After stirring at room temperature overnight, an additional 0.205 g (3.15 mmol) of sodium azide was added and the reaction warmed to 40° C. for 4 h. The reaction was cooled to room temperature, treated with saturated sodium carbonate (aq) and extracted with ethyl acetate (3×). The organic extracts were combined, washed with water (1×) and brine (1×), dried over sodium sulfate and concentrated to dryness in vacuo to give 1.2 g of a crude oil. Flash chromatography on silica gel (20% ethyl acetate in hexane) gave benzyl 2-(2-azidoethyl)benzylcarbamate as a colorless oil: 1H NMR (CDCl3, 400 MHz): δ7.39-7.20 (m, 9H), 5.14 (s, 2H), 5.05 (br s, 1H), 4.42 (d, 2H, J=5.6 Hz), 3.56-3.49 (t, 2H, J=7.0 Hz), 2.91 (t, 2H, J=7.0 Hz); MS (Electrospray): M+Na=333.1; TLC Rf=0.32 (20% ethyl acetate in hexane).

Workup

  1. temperaturethe reaction warmed to 40° C. for 4 h
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with ethyl acetate (3×)
  4. washwashed with water (1×) and brine (1×)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to dryness in vacuo
  7. customto give 1.2 g of a crude oil

Sources & evidence

ORD record
ord-66169710f15d4eafa2ad44682cd5aa80
Source dataset
uspto-grants-2003_08
Patent number
US06610701B2

Reaction notes

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