Diisopropylethylamine → HCID 86746936, compound

HRID 1587602Notes

Reaction equation

HRID 1587602 reaction equation
O.O[N:3]1[C:7]2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C.Cl.CN(C)CCCN=C=NCC.[O:33]=[C:34]([NH:43][C@H:44]([C:49]([NH:51][CH:52]([CH2:61][CH:62]1[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]1)[CH:53]([P:55](CC)([O:57][CH3:58])=[O:56])[OH:54])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])[CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C)C=O>[CH:62]1([CH2:61][C@H:52]([NH:51][C:49](=[O:50])[C@H:44]([CH2:45][CH:46]([CH3:47])[CH3:48])[NH:43][C:34](=[O:33])[CH2:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:53]([P:55]([NH:3][CH3:7])(=[O:56])[O:57][CH3:58])[OH:54])[CH2:67][CH2:66][CH2:65][CH2:64][CH2:63]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 70090484HCID 70090484, compound

Product 1

HCID 86746936HCID 86746936, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole hydrate (225 mg, 1.47 mmol), N,N-diisopropylethylamine (237.8 μl, 1.365 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (281.8 mg, 1.47 mmol) were sequentially added to a solution of the title B compound obtained from the previous reaction and the title B compound from Example 17 (276 mg, 1.26 mmol) in 5 ml dimethylformamide of 0°. The reaction mixture was warmed and stirred at room temperature for 24 hours after which it was concentrated, then treated with 30 ml pH=4.01 buffer and extracted with ethyl acetate (3×25 ml). The combined organic extracts were washed sequentially with saturated NaHCO3 (2×20 ml). Saturated NaCl (1×15 ml), dried and concentrated to give 398 mg crude product. Chromatographic purification (40 g silica gel, 1:1 hexane/ethyl acetate followed by 30:1 CHCl3 /MeOH) yielded 320 mg (60%) pure title compound. It was crystallized from ethyl acetate, m.p.=175°-177° C., [α[D =-74° (c=0.64, CH3OH) and characterized by MS, IR, 1H NMR, 13C NMR and 31P NMR [30.8 and 30.65 ppm (1.5:1.0) w.r.t. H3PO4 as external reference, CDCl3, 36.5 MHz].

Workup

  1. customobtained from the previous reaction
  2. temperatureThe reaction mixture was warmed
  3. concentrationwas concentrated
  4. additiontreated with 30 ml pH=4.01 buffer
  5. extractionextracted with ethyl acetate (3×25 ml)
  6. washThe combined organic extracts were washed sequentially with saturated NaHCO3 (2×20 ml)
  7. dry with materialSaturated NaCl (1×15 ml), dried
  8. concentrationconcentrated
  9. customto give 398 mg crude product
  10. customChromatographic purification (40 g silica gel, 1:1 hexane/ethyl acetate followed by 30:1 CHCl3 /MeOH)

Sources & evidence

ORD record
ord-c3fdfb89e5964f9fbdf0b6a2d6e101d5
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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