Methanol → HCID 86610041, compound

HRID 1375320Notes

Reaction equation

HRID 1375320 reaction equation
[C@@H:1]1([N:9]2[C:13]3[N:14]=[N:15][N:16]=[C:17]([N:18]=CN(C)C)[C:12]=3[N:11]=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1.CO[CH:25](OC)[N:26]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:28][CH2:29][CH3:30].C(Cl)Cl.CO.CO>O>[C@@H:1]1([N:9]2[C:13]3[N:14]=[N:15][N:16]=[C:17]([N:18]=[CH:25][N:26]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:31][CH2:32][CH2:33][CH3:34])[C:12]=3[N:11]=[CH:10]2)[O:6][C@H:5]([CH2:7][OH:8])[C@@H:3]([OH:4])[CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11275722N,N-di-n-butylformamide dimethyl acetalHCID 21226129Dichloromethane methanolHCID 86610040HCID 86610040, compound

Product 1

HCID 86610041HCID 86610041, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As described for 9a but using N,N-di-n-butylformamide dimethylacetal. Colorless needles (75%). M.p. 107–109° C. TLC (silica gel, CH2Cl2—MeOH, 9:1): Rf 0.42. UV: (10% MeOH in water): λmax 235 (10200), 325 nm (25700). 1H NMR ([D6]DMSO): δ 0.93 (t, 6H, CH3), 1.33, 1.64, 3.70 (3m, 12H, —CH2—); 2.45, 2.80 (2m, 2H, H2—C(2′)); 3.60 (m, 2H, H2—C(5′)); 3.92 (m, 1H, H—C(4′)); 4.48 (m, 1H, H C(3′)); 5.04 (t, 1H, 3J(H,H)=5.8 Hz, 5′-OH); 5.39 (d, 1H, 3J(H,H)=4.0 Hz, 3′-OH); 6.55 (pt, 1H, 3J(H,H)=6.3 Hz, H—C(1′)); 8.78 (s, 1H, N═CH); 9.08 (s, 1H, H—C(8)). Anal. calcd. for C18H29N7O3 (391.5): C 55.23; H 7.47; N 25.05; found: C 55.36, H 7.66, N 24.97.

Sources & evidence

ORD record
ord-eec9d06b4f834661bcc68d9ebc9f94f0
Source dataset
uspto-grants-2007_01
Patent number
US07169553B1

Reaction notes

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