4-Methylmorpholine → HCID 23257312, compound

HRID 279730Notes

Reaction equation

HRID 279730 reaction equation
[C:1]([OH:16])(=O)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].[B-](F)(F)(F)F.CC[O:24]C(C(C#N)=NOC(N(C)C)=[N+](C)C)=O.CN1CCOCC1.C1C2C(COC([NH:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][O:70][CH2:71][C@H:72]3[O:76][C@@H:75]([N:77]4[C:100]5[N:99]=[CH:98][N:97]=[C:81]([NH:82]C(OCCC6C=CC([N+]([O-])=O)=CC=6)=O)[C:80]=5[N:79]=[CH:78]4)[C@H:74]([O:101]C(OCCC4C=CC([N+]([O-])=O)=CC=4)=O)[CH2:73]3)=O)C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CN(C=O)C>[C:1]([NH:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][C:69]([O:70][CH2:71][C@H:72]1[O:76][C@@H:75]([N:77]2[C:100]3[N:99]=[CH:98][N:97]=[C:81]([NH2:82])[C:80]=3[N:79]=[CH:78]2)[C@H:74]([OH:101])[CH2:73]1)=[O:24])(=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 8082PiperidineHCID 11005Myristic AcidHCID 516892Sodium BicarbonateHCID 2733286O-[(Ethoxycarbonyl)cyanomethylenamino]-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86757910HCID 86757910, compound

Product 1

HCID 23257312HCID 23257312, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

As described in Preparation 4, with tetradecanoic acid (151 mg, 0.66 mmol), TOTU (67 mg, 0.66 mmol), and N-methylmorpholine (67, 0.66 mmol) in abs. DMF (3 ml; 1 h). Deblocking of 7 (584 mg, 0.6 mmol) with 3% piperidine in abs. DMF (6 ml; 10 min) and addition of above-mentioned soln. (r.t., 2.5 h). Workup with CHCl3 (150 ml) and NaHCO3 soln. (2×70 ml) and reextraction. Purification by FC (silica gel, 12×3 cm, CHCl3, then CHCl3/MeOH 98:2,95:5): 405 mg (70%) of 14. Colorless oil. 1H-NMR (CDCl3): 8.73-8.15 (m, H—C(8), H—C(2), 4 H o to NO2, NH(ade)); 7.47-7.38 (m, 4H m to NO2); 6.12 (d, H—C(1′)); 5.73 (m, H—C(2′)); 5.57 (t, NH(CH2)5CO); 4.68 (m, H—C(4′)); 4.54, 4.43 (2t, 2 OCH2CH2); 4.4-4.2 (m, 2 H—C(5′)); 3.7-3.5 (m, 1 CH2 of NH(CH2)5CO); 3.25-3.1 (m, 2 OCH2CH2, 1 CH2 of NH(CH2)5CO); 2.65, 2.25 (2m, 2 H—C(3′)); 2.27, 2.15 (2t, 2 CH2 of NH(CH2)5CO), 1 CH2 of Me(CH2)12CO); 1.7-1.15 (m, 3 CH2 of NH(CH2)5CO), 11 CH2 of Me(CH2)12CO); 0.87 (t, Me(CH2)12CO).

Workup

  1. custom(r.t., 2.5 h)
  2. customPurification by FC (silica gel, 12×3 cm, CHCl3

Sources & evidence

ORD record
ord-c61e2f1a272945c08516afe07874df97
Source dataset
uspto-grants-2002_03
Patent number
US06362171B1

Reaction notes

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