Sodium hydride → 18-(tert-Butoxycarbonyl)-6,12,18-tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrile

HRID 1109845

Reaction equation

HRID 1109845 reaction equation
[C:1]([O:5][C:6]([NH:8][O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].C(O[C:24]([N:26]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:47])[N:32]([O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:33][CH2:34][CH2:35][CH2:36][C:37]#[N:38])=[O:25])(C)(C)C.[CH3:56][CH2:57][CH2:58][CH2:59]CC.CCOC(C)=O>CN(C=O)C>[C:1]([O:5][C:6]([N:8]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:56][CH2:57][CH2:58][CH2:59][C:24](=[O:25])[N:26]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[CH2:27][CH2:28][CH2:29][CH2:30][C:31](=[O:47])[N:32]([O:39][CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[CH2:33][CH2:34][CH2:35][CH2:36][C:37]#[N:38])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 736159Tert-butyl N-(benzyloxy)carbamateHCID 1032403412-(tert-Butoxycarbonyl)-6,12-bis(benzyloxy)-7-oxo-6,12-diazadodecanenitrileHCID 21226206Ethyl acetate hexane

Product 1

HCID 1048499118-(tert-Butoxycarbonyl)-6,12,18-tris(benzyloxy)-7,13-dioxo-6,12,18-triazaoctadecanenitrileYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(tert-Butoxycarbonyl )-O-benzylhydroxylamine (1.43 g, 6.40 mmol) was alkylated with (6) (3.00 g, 5.68 mmol) using NaH (80%, 0.19 g, 6.33 mmol) in DMF (100 mL), following the procedure used for (4). Column chromatography on silica gel with 4:1 hexane/EtOAc yielded 3.0 g (74%) of (7) as an oil: NMR δ 1.50 (s, 9 H), 1.40-1.85 (m, 12 H), 2.20-2.50 (m, 6 H), 3.27-3.70 (m, 6 H), 4.75 (s, 6 H), 7.33 (s, 15 H). Anal. (C41H54N4O7) C, H, N.

Sources & evidence

ORD record
ord-00af994a3d514c75a88b6af4ed389672
Source dataset
uspto-grants-1994_06
Patent number
US05322961

Linked notes

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