Sodium Hydroxide → HCID 21901078, compound

HRID 719666Notes

Reaction equation

HRID 719666 reaction equation
[N+:1]([C:4]1[CH:76]=[CH:75][C:7]([CH2:8][CH:9]2[CH2:26][N:25]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23][N:22]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:21][CH2:20][N:19]([CH2:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[CH2:18][CH2:17][N:16]([CH2:51][C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:15][CH2:14][N:13]([CH2:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:12][CH2:11][N:10]2[CH2:67][C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])=[CH:6][CH:5]=1)([O-])=O.Cl[Sn]Cl.[OH-].[Na+]>C(O)C.O>[NH2:1][C:4]1[CH:76]=[CH:75][C:7]([CH2:8][CH:9]2[CH2:26][N:25]([CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])[CH2:24][CH2:23][N:22]([CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:21][CH2:20][N:19]([CH2:43][C:44]([O:46][C:47]([CH3:48])([CH3:49])[CH3:50])=[O:45])[CH2:18][CH2:17][N:16]([CH2:51][C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])[CH2:15][CH2:14][N:13]([CH2:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])[CH2:12][CH2:11][N:10]2[CH2:67][C:68]([O:70][C:71]([CH3:74])([CH3:73])[CH3:72])=[O:69])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 9963786HCID 9963786, compound

Product 1

HCID 21901078HCID 21901078, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-(4-nitrobenzyl)-1,4,7,10,13,16-hexakis(tert-butoxycarbonylmethyl) -1,4,7,10,13,16-hexaazacycloocta (6) (15 mmol) in ethanol (50 ml) at room temperature under a nitrogen atmosphere was added SnCl2 (0.125 mol). The mixture was refluxed for 12 hours after which the solvent was removed and the compound thus obtained was dissolved in water; the solution was brought to pH 8 with 2M NaOH. The resulting precipitate was removed off and the filtrate concentrated on vacuum; the residue was dissolved in acetonitrile and passed over Celite. The filtrate was evaporated on vacuum to give yellow oil. The yield was 62%.

Workup

  1. temperatureThe mixture was refluxed for 12 hours after which the solvent
  2. customwas removed
  3. customthe compound thus obtained
  4. customThe resulting precipitate was removed off
  5. concentrationthe filtrate concentrated on vacuum
  6. dissolutionthe residue was dissolved in acetonitrile
  7. customThe filtrate was evaporated on vacuum
  8. customto give yellow oil

Sources & evidence

ORD record
ord-2be79ffa2b4647cebe5aae9987852fdf
Source dataset
uspto-grants-2006_11
Patent number
US07132513B2

Reaction notes

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