Diisopropylethylamine → HCID 86746935, compound

HRID 1587600Notes

Reaction equation

HRID 1587600 reaction equation
OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.[O:32]=[C:33]([NH:42][C@H:43]([C:48]([NH:50][CH:51]([CH2:60][CH:61]1[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]1)[CH:52]([P:54]([CH2:58]C)([O:56][CH3:57])=[O:55])[OH:53])=[O:49])[CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>CN(C)C=O>[CH:61]1([CH2:60][C@H:51]([NH:50][C:48](=[O:49])[C@H:43]([CH2:44][CH:45]([CH3:46])[CH3:47])[NH:42][C:33](=[O:32])[CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:52]([P:54]([CH3:58])(=[O:55])[O:56][CH3:57])[OH:53])[CH2:66][CH2:65][CH2:64][CH2:63][CH2:62]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 70090484HCID 70090484, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 86746935HCID 86746935, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydroxybenzotriazole 85.7 mg, 0.56 mmol), diisopropylethylamine (90.6 μl, 0.52 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (107.3 mg, 0.56 mmol) were sequentially added to a solution of the title D compound (114.2 mg, 0.4 mmol) and compound B from Example 17 (126.2 mg, 0.48 mmol) in 2 ml dimethylformamide at 0°. The reaction mixture was warmed and stirred at room temperature for 60 hours after which it was concentrated, then treated with 15 ml pH=4.01 buffer and extracted with ethyl acetate (3×25 ml). Drying and concentration gave 425 mg crude product which after flash chromatographic purification (20 g silica gel, 19:1 CHCl3 /MeOH) gave 146 mg (74%) of the title compound Isomer A which was characterized by MS, IR, 1H NMR and 13C NMR. After repeated chromatography and finally, crystallization from hexane/ethyl acetate, the title compound Isomer A (56 mg) was obtained, m.p. 165°-170° C. [α]D =-67.1° (c=0.66, CH3OH).

Workup

  1. temperatureThe reaction mixture was warmed
  2. concentrationwas concentrated
  3. additiontreated with 15 ml pH=4.01 buffer
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. customDrying
  6. concentrationconcentration
  7. customgave 425 mg crude product which
  8. customafter flash chromatographic purification (20 g silica gel, 19:1 CHCl3 /MeOH)

Sources & evidence

ORD record
ord-1edbd142437748418a42def3f7de9c87
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

Loading…