Sodium Carbonate → HCID 18672407, compound

HRID 1058221Notes

Reaction equation

HRID 1058221 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:12]=1[CH2:13]O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC(P([N:34]=[N+:35]=[N-:36])(C2C=CC=CC=2)=O)=CC=1.[CH2:37]1[CH2:47][CH2:46]N2C(=NCCC2)CC1.[C:48](=O)([O-])[O-].[Na+].[Na+]>C1COCC1>[C:47]([CH:13]([N:36]=[N+:35]=[N-:34])[C:12]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:11]=1[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])([CH3:37])([CH3:48])[CH3:46]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 23000593HCID 23000593, compound

Product 1

HCID 18672407HCID 18672407, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 649 mg (2.27 mmol) 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl alcohol from the previous step in 5.0 mL THF at 0° C. was added 0.674 mL (3.13 mmol) of DPPA and 0.468 mL (3.13 mmol) of DBU and the reaction was stirred at 0° C. for 10 min, then at room temperature. After 3 h the reaction was treated with saturated aqueous sodium carbonate and extracted with ethyl acetate (3×). The organic extracts were combined, washed with brine, dried over sodium sulfate, filtered and concentrated to dryness in vacuo to give 963 mg of a crude oil. Flash chromatography on silica gel (15% ethyl acetate in hexane) gave tert-butyl 2-(2-(tert-butoxycarbonylamino)ethyl)-5-chlorobenzyl azide as a colorless oil: 1H NMR (DMSO-d6, 400 MHz): δ 7.44 (d, 1H, J=1.8 Hz), 7.36 (dd, 1H, J=2.0 and 8.2 Hz), 7.26 (d, 1H, J=8.1 Hz), 6.92 (br t, 1H, J=5.5 Hz), 4.53 (s, 2H), 3.10 (dt, 2H, J=6.3 and 7.6 Hz), 2.73 (t, 2H, J=7.3 Hz), 1.36 (s, 9H); MS (Electrospray): M+Na=333.0; TLC Rf=0.32 (15% ethyl acetate in hexane).

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate (3×)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness in vacuo
  7. customto give 963 mg of a crude oil

Sources & evidence

ORD record
ord-d9ec1f530db242298b018839fb24e08b
Source dataset
uspto-grants-2003_02
Patent number
US06515011B2

Reaction notes

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