HCID 68454230, compound → HCID 68454833, compound

HRID 2085813Notes

Reaction equation

HRID 2085813 reaction equation
[CH3:1][N:2]([CH3:59])[CH2:3][CH2:4][C@@H:5]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:40]4[CH2:45][CH2:44][N:43](C(OC(C)(C)C)=O)[CH2:42][C:41]4=[O:53])=[CH:35][C:34]=3[O:54][CH3:55])=[CH:29][CH:28]=2)=[O:26])(=[O:23])=[O:22])=[CH:17][C:16]=1[N+:56]([O-:58])=[O:57])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>O1CCOCC1.Cl>[CH3:59][N:2]([CH3:1])[CH2:3][CH2:4][C@@H:5]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]([C:27]2[CH:28]=[CH:29][C:30]([C:33]3[CH:38]=[CH:37][C:36]([CH2:39][N:40]4[CH2:45][CH2:44][NH:43][CH2:42][C:41]4=[O:53])=[CH:35][C:34]=3[O:54][CH3:55])=[CH:31][CH:32]=2)=[O:26])(=[O:22])=[O:23])=[CH:17][C:16]=1[N+:56]([O-:58])=[O:57])[CH2:6][S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 1

HCID 68454230HCID 68454230, compound

Product 1

HCID 68454833HCID 68454833, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of Example 500F (73 mg, 0.09 mmol) in dioxane (1 mL) and 4M HCl (1 mL) at room temperature was stirred for 16 hours, and purified by flash column chromatography on silica gel with 80:20:0.5 dichloromethane/methanol/concentrated ammonium hydroxide to provide the desired product. MS (ESI) m/e 745, 747 (M−H)−, (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ2.07 (m, 2H), 2.54 (d, 6H), 2.74 (m, 1H), 3.04 (m, 2H), 3.17 (d, 2H), 3.23 (t, 2H), 3.32 (t, 2H), 3.47 (s, 2H), 3.74 (s, 3H), 4.09 (m, 1H), 4.54 (s, 2H), 6.89-6.99 (m, 3H), 7.17 (tt, 2H), 7.22-7.34 (m, 4H), 7.39 (d, 2H), 7.81 (dd, 1H), 7.88 (dd, 2H), 8.21 (d, 1H), 8.47 (d, 1H).

Workup

  1. custompurified by flash column chromatography on silica gel with 80:20:0.5 dichloromethane/methanol/concentrated ammonium hydroxide

Sources & evidence

ORD record
ord-7f97937e43354620be66e59e378b5c81
Source dataset
uspto-grants-2004_04
Patent number
US06720338B2

Reaction notes

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