HCID 135452396, compound → HCID 136380187, compound

HRID 1092857Notes

Reaction equation

HRID 1092857 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]3[NH:14][C:13]([C:15]([C:50]4[C:55]([CH3:56])=[CH:54][C:53]([CH3:57])=[CH:52][C:51]=4[CH3:58])=[C:16]4[N:49]=[C:19]([C:20]([C:41]5[CH:46]=[CH:45][C:44]([CH2:47][OH:48])=[CH:43][CH:42]=5)=[C:21]5[NH:40][C:24](=[C:25]([C:31]6[C:36]([CH3:37])=[CH:35][C:34]([CH3:38])=[CH:33][C:32]=6[CH3:39])[C:26]6[CH:27]=[CH:28][C:29]=2[N:30]=6)[CH:23]=[CH:22]5)[CH:18]=[CH:17]4)=[CH:12][CH:11]=3)=[CH:5][CH:4]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)Cl.C(Cl)(Cl)Cl>[CH:47]([C:44]1[CH:45]=[CH:46][C:41]([C:20]2[C:21]3[NH:40][C:24]([C:25]([C:31]4[C:32]([CH3:39])=[CH:33][C:34]([CH3:38])=[CH:35][C:36]=4[CH3:37])=[C:26]4[N:30]=[C:29]([C:9]([C:6]5[CH:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=5)=[C:10]5[NH:14][C:13](=[C:15]([C:50]6[C:51]([CH3:58])=[CH:52][C:53]([CH3:57])=[CH:54][C:55]=6[CH3:56])[C:16]6[CH:17]=[CH:18][C:19]=2[N:49]=6)[CH:12]=[CH:11]5)[CH:28]=[CH:27]4)=[CH:23][CH:22]=3)=[CH:42][CH:43]=1)=[O:48]

Participants

5

Reactant 2

HCID 135452396HCID 135452396, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 136380187HCID 136380187, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 15 (0.190 g, 0.250 mmol) in CH2Cl2 (25 mL) was treated with pyridinium chlorochromate (216 mg, 1.00 mmol). The reaction mixture was stirred at room temperature and monitored by TLC. After 90 min, the reaction mixture was poured on to a silica column (poured in CHCl3) and eluted with CHCl3/methanol (95:5) affording a purple solid (156 mg, 83%): 1H NMR δ −2.63 (brs, 2H), 1.84 (s, 12H), 2.63 (s, 6H), 7.29 (s, 4H), 8.28 (d, J=8.4 Hz, 4H), 8.41 (d, J=8.4 Hz, 4H), 8.71-8.78 (m, 8H), 10.39 (s, 2H); LD-MS obsd 755.24, calcd 754.3308 (C52H42N4O2); λabs 422, 515, 549, 594, 649 nm.

Workup

  1. washeluted with CHCl3/methanol (95:5)

Sources & evidence

ORD record
ord-b67d23492b444c5cbd9fa0ea39fee8b4
Source dataset
uspto-grants-2012_03
Patent number
US08129520B2

Reaction notes

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