N-Iodosuccinimide → HCID 10984692, compound

HRID 1018038Notes

Reaction equation

HRID 1018038 reaction equation
Cl[C:2]1[C:10]2[C:9]([O:11][CH3:12])=[N:8][C:7]([NH:13][CH:14]=[O:15])=[N:6][C:5]=2[N:4]([C@@H:16]2[O:26][C@H:25]([CH2:27][O:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[C@@H:18]([O:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])[CH2:17]2)[CH:3]=1.CC(C)C(O[C@@H]1[C@@H](COC(=O)C(C)C)O[C@@H](C2C3C(OC)=NC(NC=O)=NC=3NC=2)C1)=O.[I:66]N1C(=O)CCC1=O>C1CCCCC1>[CH3:22][CH:21]([CH3:23])[C:20]([O:19][C@@H:18]1[C@@H:25]([CH2:27][O:28][C:29](=[O:33])[CH:30]([CH3:32])[CH3:31])[O:26][C@@H:16]([N:4]2[C:5]3[N:6]=[C:7]([NH:13][CH:14]=[O:15])[N:8]=[C:9]([O:11][CH3:12])[C:10]=3[C:2]([I:66])=[CH:3]2)[CH2:17]1)=[O:24]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 15218404HCID 15218404, compoundHCID 131723638HCID 131723638, compound

Product 1

HCID 10984692HCID 10984692, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

Compound (46) is prepared as described for compound (45) by proceeding from compound (18) (500 mg, 1.11 mmol) and N-iodosuccinimide (264 mg, 1.16 mmol). The duration of the reaction is 23 h. Colorless crystals (590 mg, 92%) are obtained from cyclohexane. 1H-NMR ([D6] DMSO): δ=1.9 (d, J=7.0, CH3), 1.15 (d, J=7.0, CH3), 2.46, 2.60, 2.89 (3 m, CH and Hα,β—C(2′)), 4.06 (s, OCH3), 4.17 (m, H—C(5′)), 4.27 (m, H—C(4′)), 5.35 (m, H—C(3′)), 6.46 (m, H—C(1′)), 7.62 (8, H—C(6)), 9.55 (d, J=9.7, NH), 10.81 (d, J=9.9 HCO). Anal. calculated for C21H27JN4O7 (574.4): C 43.91, H 4.74, N 9.75; found: C 43.98, H 4.75, N 9.82.

Sources & evidence

ORD record
ord-6aab3cda7fc7449bb1b883d1b6171015
Source dataset
uspto-grants-2002_11
Patent number
US06479651B1

Reaction notes

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