Triethylamine → HCID 22464027, compound

HRID 1935625Notes

Reaction equation

HRID 1935625 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]3[CH2:24][CH:23]([CH2:25]O)[O:22][C:21]3=[O:27])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:39](CC)CC)C.[N+](C1C=C(S(Cl)(=O)=O)C=CC=1)([O-])=O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([N:20]3[CH2:24][CH:23]([CH2:25][NH2:39])[O:22][C:21]3=[O:27])=[CH:17][CH:18]=2)[CH2:13][CH:12]1[CH2:28][O:29][Si:30]([C:33]([CH3:34])([CH3:35])[CH3:36])([CH3:31])[CH3:32])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 22464066HCID 22464066, compound

Product 1

HCID 22464027HCID 22464027, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
55 °C

Procedure

An ice cold, stirred mixture of the product from Step 6 (6.03 g, 0.0117 mol) and triethylamine (4.55 ml) in methylene chloride (340 ml) is treated, portionwise during 10 min, with 3-nitrobenzenesulfonyl chloride (3.2 g) and kept in the ice bath for 15 min. It is then kept at ambient temperature for 16 h, diluted with CH2Cl2, washed with saturated NaHCO3 and brine, dried (MgSO4) and concentrated. A stirred solution of the residue (9.32 g) in a mixture of 2-propanol (250 ml), acetonitrile (250 ml), and concentrated ammonium hydroxide (250 ml) is warmed at 55° C. under a dry ice-acetone condenser for 3.5 h and kept at ambient temperature for 18 h. Additional ammonium hydroxide (50 ml) is added; the mixture is warmed at 55° C. for 30 min, kept at ambient temperature for 3 d and concentrated in vacuo. The aqueous residue is extracted with methylene chloride. The extract is washed water and brine, dried (Na2SO4) and concentrated to give 6.53 g of the titled product: 1H NMR (300 MHz, CDCl3) δ−0.11 (s, 3H), −0.06 (s, 3H), 0.76 (s, 9H), 3.03 (m, 3H), 3.24 (m, 1H), 3.79 (m, 2H), 4.02 (m, 2H), 4.52 (broad s, 1H), 4.65 (m, 1H), 5.27 (m, 2H), 7.08 (m, 1H), 7.38 (m, 5H), 7.62, 7.79 (broad s, 2H).

Workup

  1. washwashed with saturated NaHCO3 and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. additionA stirred solution of the residue (9.32 g) in a mixture of 2-propanol (250 ml), acetonitrile (250 ml), and concentrated ammonium hydroxide (250 ml)
  5. waitkept at ambient temperature for 18 h
  6. additionAdditional ammonium hydroxide (50 ml) is added
  7. temperaturethe mixture is warmed at 55° C. for 30 min
  8. waitkept at ambient temperature for 3 d
  9. concentrationconcentrated in vacuo
  10. extractionThe aqueous residue is extracted with methylene chloride
  11. washThe extract is washed water and brine
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-dfd33b402fea4c2b89bf52032cea9484
Source dataset
uspto-grants-2002_05
Patent number
US06387896B1

Reaction notes

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