Diisopropylethylamine → HCID 66868028, compound

HRID 1994371Notes

Reaction equation

HRID 1994371 reaction equation
[C:1]([O:5][C:6](=[O:12])[CH2:7][C@H:8]([NH2:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH2:13]([O:20][C:21]([N:23]1[C@H:28]([C:29](O)=[O:30])[C@@H:27]2[CH2:32][C@H:24]1[CH2:25][CH2:26]2)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O.ON1N=C2C=CC=CC2=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>C1COCC1.CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[CH2:13]([O:20][C:21]([N:23]1[C@H:28]([C:29](=[O:30])[NH:11][C@H:8]([CH2:9][OH:10])[CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:12])[C@@H:27]2[CH2:32][C@H:24]1[CH2:25][CH2:26]2)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

9

Reactant 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18326971HCID 18326971, compoundHCID 59136378HCID 59136378, compoundHCID 67561008HCID 67561008, compound

Product 1

HCID 66868028HCID 66868028, compoundYield 91.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (S)-3-Amino-4-hydroxy-butyric acid tert-butyl ester (486 mg) and (1R,3S,4S)-2-Aza-bicyclo[2.2.l]heptane-2,3-dicarboxylic acid 2 benzyl ester (prepared as described in Tararov etal, Tett. Asymm. 2002, 13, 25-28) (767 mg) in THF (18 ml) was added 2-hydroxybenzotriazole hydrate (452 mg), DMAP (426 mg), diisopropylethylamine (631□1) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 641 mg). The resulting mixture was stirred at ambient temperature for 18 hours then diluted with ethyl acetate. The mixture was then washed with water, saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (60% ethyl acetate/petrol) to afford the sub-title compound as a colorless oil (1.1 g, 91%); 1H NMR (400 MHz, d-6 DMSO) δ 1.13-1.25 (1H, m), 1.30-1.48 (9H, m), 1.49-1.88 (6H, m), 2.20-2.52 (2H, m), 3.09-3.34 (2H, m), 3.64 (1H, d), 4.00-4.16 (2H, brm), 4.80 (1H, m), 4.90-5.15 (2H, m), 7.21-7.41 (5H, m), 7.50-7.75 (1H, m); MS ES (+) 433.37.

Workup

  1. washThe mixture was then washed with water, saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (60% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-11a2ff65864a405eaf42978d23f9cab7
Source dataset
uspto-grants-2010_01
Patent number
US07652153B2

Reaction notes

Loading…