p-Toluenesulfonic acid → HCID 8883831, compound

HRID 963511Notes

Reaction equation

HRID 963511 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.[N+:32]([C:35]1[CH:36]=[C:37]([CH:41]=[CH:42][CH:43]=1)[C:38](Cl)=[O:39])([O-:34])=[O:33]>C(Cl)Cl>[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH:22][C:38](=[O:39])[C:37]1[CH:41]=[CH:42][CH:43]=[C:35]([N+:32]([O-:34])=[O:33])[CH:36]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 726858benzyl (2S)-2-aminopropanoate

Product 1

HCID 8883831HCID 8883831, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of p-toluenesulfonic acid salt of L-alanine benzyl ester (7.03 g, 0.02 mol) and triethylamine (4.55 g, 0.045 mol) in methylene chloride (80 ml) was added dropwise a solution of 3-nitrobenzoyl chloride (3.71 g, 0.02 mol) in methylene chloride (20 ml) under ice-cooling and stirring. After the addition was completed, the mixture was stirred for 0.5 hour under the same condition and for 0.5 hour at ambient temperature. The mixture was washed with diluted hydrochloric acid and water twice successively. After drying over MgSO4, the solvent was removed in vacuo to give N-(3-nitrobenzoyl)-L-alanine benzyl ester (6.54 g, 99.6% yield) as a colorless crystal, which was used in a following reaction without further purification. 1H-NMR (CDCl3, δ): 1.56 (3H, d, J=7.2 Hz), 4.86 (1H, q, J=7.2 Hz), 5.24 (2H, dd, J=12.3 Hz, 13.6 Hz), 6.98 (1H, br, d, J=7.0 Hz), 7.37 (5H, s), 7.63 (1H, t, J=8.0 Hz), 8.14 (1H, dd, J=1.2Hz, 8.0 Hz), 8.35 (1H, d, t, J=8.0 Hz, 0.92 Hz), 8.62 (1H, t, J=0.92 Hz); APCI-MS: 329 (M+ +1)

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe mixture was stirred for 0.5 hour under the same condition and for 0.5 hour at ambient temperature
  4. washThe mixture was washed with diluted hydrochloric acid and water twice successively
  5. dry with materialAfter drying over MgSO4
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-778c302ddefb435aa3ee10c0319cd32d
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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