Triethylamine → HCID 18957773, compound

HRID 2379336Notes

Reaction equation

HRID 2379336 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]2[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=2[N:4]([CH2:18][CH3:19])[C:3]1=[O:20].C(N(CC)CC)C.Cl[C:29]([O:31][C:32]1[CH:37]=[CH:36][C:35]([N+:38]([O-:40])=[O:39])=[CH:34][CH:33]=1)=[O:30]>O1CCCC1>[CH:9]1([C:7]2[C:6]3[CH:14]=[CH:15][CH:16]=[CH:17][C:5]=3[N:4]([CH2:18][CH3:19])[C:3](=[O:20])[CH:2]([NH:1][C:29]([O:31][C:32]3[CH:33]=[CH:34][C:35]([N+:38]([O-:40])=[O:39])=[CH:36][CH:37]=3)=[O:30])[N:8]=2)[CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 821294-Nitrophenyl chloroformateHCID 18957776HCID 18957776, compound

Product 1

HCID 18957773HCID 18957773, compoundYield 79.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of crude 3(R,S)-amino-5-cyclopentyl-l,3-dihydro-1-ethyl-2H-1, 4-benzodiazepin-2-one [Example 5, Step 5] (0.23 g, 0.92 mmol) in dry tetrahydrofuran (15 ml) under an atmosphere of nitrogen, at 0° C., was treated with triethylamine (0.11 ml, 0.92 mmol) followed by a solution of 4-nitrophenyl chloroformate (184 mg, 0.92 mmol) in tetrahydrofuran (10 ml). After stirring at ambient temperature for 30 min the solid which precipitated was removed by filtration and the tiltrate concentrated in vacuo to afford the title compound (0.32 g, 79%) as a colourless solid. mp 136°-138° C. 1H NMR (360 MHz, CDCl3) δ 0.9 (3H, t, J=7 Hz), 1.0-2.2 (8H,m), 3.50 (1H, p, J=7 Hz), 3.70 (1H, m), 4.18-4.28 (1H, m), 5.14 (1H, d, J=8 Hz), 7.30-8.20 (8H, m), 9.12 (1H, d, J=8 Hz).

Workup

  1. customprecipitated
  2. customwas removed by filtration
  3. concentrationthe tiltrate concentrated in vacuo

Sources & evidence

ORD record
ord-af2525185ee74c7e93d6f16f4da551cd
Source dataset
uspto-grants-1994_11
Patent number
US05360802

Reaction notes

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