Diisopropylethylamine → HCID 86746935, compound

HRID 1587601Notes

Reaction equation

HRID 1587601 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, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydroxybenzotriazole (120 mg, 0.784 mmol), diisopropylethylamine (127 μl, 0.728 mmol) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (150 mg, 0.784 mmol) were sequentially added to a solution of the title A compound obtained from the previous reaction and the title B compound from Example 17 (176.7 mg, 0.672 mmol) in 3 ml dimethylformamide at 0°. The reaction mixture was warmed and stirred at room temperature for 72 hours after which it was concentrated, then treated with 20 ml pH=4.01 buffer and extracted with ethyl acetate (3×30 ml). Drying and concentration followed by chromatographic purification of the crude product gave 146 mg 52.7%) pure title compound lsomer B, m.p. 188°-207°, [α]D =-71.7° (c=0.545, CH3OH) which was characterized by MS, IR, 1H NMR, 13C NMR and 31P NMR [56.0 ppm w.r.t H3PO4 as external reference, CDCl3, 36.4 MHz].

Workup

  1. customobtained from the previous reaction
  2. customat 0°
  3. temperatureThe reaction mixture was warmed
  4. concentrationwas concentrated
  5. additiontreated with 20 ml pH=4.01 buffer
  6. extractionextracted with ethyl acetate (3×30 ml)
  7. customDrying
  8. concentrationconcentration
  9. customfollowed by chromatographic purification of the crude product

Sources & evidence

ORD record
ord-90395a46cb934c44bbe21aeb43688b5a
Source dataset
uspto-grants-1993_06
Patent number
US05217958

Reaction notes

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