Carbon Dioxide → HCID 58909210, compound

HRID 1295611Notes

Reaction equation

HRID 1295611 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH3:6][CH2:7][CH2:8]CC.[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20].[C:24](=[O:26])=O.C([NH2:34])C1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C>[CH2:2]([NH:34][C:24]([C:13]1[CH:14]=[CH:15][O:11][C:12]=1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:26])[C:1]1[CH:4]=[CH:8][CH:7]=[CH:6][CH:3]=1

Participants

10

Reactant 8

HCID 280Carbon DioxideHCID 7504BenzylamineHCID 8003PentaneHCID 8471TriethylamineHCID 181649HOAtHCID 317628Tert-butyl n-(2-furyl)carbamateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418306HCID 178418306, compound

Product 1

HCID 58909210HCID 58909210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of tert-butyllithium in pentane (2.40 equiv) is added to a solution of tert-butyl 2-furylcarbamate (prepared by the method of Padwa, et al Org Synth 2000, 78, 2002, 1 equiv) in TEF at −78° C. The reaction mixture is stirred for 45 min, then solid CO2 (excess) is added and the resulting mixture is warmed to 0° C. and stirred for 30 minutes. The reaction mixture is partitioned between aqueous 1 N hydrochloric acid solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column chromatography (hexanes initially, grading to 100% ethyl acetate), and the polar fractions are concentrated. A solution of the residue, benzylamine (2 equiv), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1 equiv), 1-hydroxy-7-azabenzotriazole (1 equiv), and triethylamine (2 equiv) in DMF is stirred at 55° C. for 24 h. The reaction mixture is concentrated, and the residue is partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column (hexanes initially, grading to 100% ethyl acetate) to give tert-butyl 3-[(benzylamino)carbonyl]-2-furylcarbamate (1-1).

Workup

  1. customprepared by the method of Padwa, et al Org Synth 2000, 78, 2002, 1 equiv) in TEF at −78° C
  2. stirringstirred for 30 minutes
  3. customThe reaction mixture is partitioned between aqueous 1 N hydrochloric acid solution and ethyl acetate
  4. dry with materialThe combined organic layers are dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue is purified by flash column chromatography (hexanes initially
  7. concentrationare concentrated
  8. concentrationThe reaction mixture is concentrated
  9. customthe residue is partitioned between saturated aqueous sodium bicarbonate solution and ethyl acetate
  10. dry with materialThe combined organic layers are dried over sodium sulfate
  11. concentrationconcentrated
  12. customThe residue is purified by flash column (hexanes initially

Sources & evidence

ORD record
ord-53dccb2481f64771a0ecccd2c2ba9e56
Source dataset
uspto-grants-2007_07
Patent number
US07244723B2

Reaction notes

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