Triethylamine → HCID 21830376, compound

HRID 1601068Notes

Reaction equation

HRID 1601068 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[CH3:20][O:21][C:22]1[CH:28]=[CH:27][C:25]([NH2:26])=[C:24]([N+:29]([O-:31])=[O:30])[CH:23]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:26][C:25]1[CH:27]=[CH:28][C:22]([O:21][CH3:20])=[CH:23][C:24]=1[N+:29]([O-:31])=[O:30])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14349BenzyloxycarbonylglycineHCID 24386Thionyl ChlorideHCID 667934-Methoxy-2-nitroaniline

Product 1

HCID 21830376HCID 21830376, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-(Benzyloxycarbonyl)glycine (2.72 g, 13.13 mmol) was dissolved in CH2Cl2 and an excess of thionyl chloride at room temperature. After 2 h, the reaction was evaporated under vacuum and the residue was stripped with toluene twice and dried under vacuum. The white solid was taken into CH2Cl2 and 4-methoxy-2-nitroaniline (2.1819 g, 12.98 mmol) was added as a solid, followed by triethylamine (2.0 mL, 1.455 g, 14.38 mmol). The reaction was stirred at RT for 24 h, then was evaporated under vacuum. The residue was dissolved in EtOAc and washed with aqueous 1N NaHCO3. The EtOAc layer was dried (MgSO4) and concentrated under vacuum. Thin layer chromatography analysis (1:1:1 hexanes/Et2O/CH2Cl2) showed good conversion to the acylated material. The crude material was dissolved in 2:1:1 hexanes/Et2O/CH2Cl2 initially, with the addition of enough Et2O/CH2Cl2 and sonication/heating to dissolve all the solid material. Silica gel chromatography (2:1:1 hexanes/Et2O/CH2Cl2 (2 L), then 1:1:1 hexanes/Et2O/CH2Cl2 (1.5 L), then Et2O/CH2Cl2) gave the title compound (3.3387 g, 72%): 1H NMR (250 MHz, CDCl3) δ 3.85 (s, 3H), 4.06 (d, 2H), 5.18 (s, 2H), 5.61 (t, 1H), 7.2-7.4 (m, 6H), 7.65 (d, 1H), 8.63 (d, 1H).

Workup

  1. customat room temperature
  2. customthe reaction was evaporated under vacuum
  3. customdried under vacuum
  4. additionwas added as a solid
  5. customwas evaporated under vacuum
  6. dissolutionThe residue was dissolved in EtOAc
  7. washwashed with aqueous 1N NaHCO3
  8. dry with materialThe EtOAc layer was dried (MgSO4)
  9. concentrationconcentrated under vacuum
  10. dissolutionThe crude material was dissolved in 2:1:1 hexanes/Et2O/CH2Cl2 initially
  11. additionwith the addition of enough Et2O/CH2Cl2
  12. temperaturesonication/heating
  13. dissolutionto dissolve all the solid material

Sources & evidence

ORD record
ord-e41eaa8d9a5844779ff2b2736d489aa0
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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