Diethyl Ether → HCID 18705601, compound

HRID 363404Notes

Reaction equation

HRID 363404 reaction equation
[CH2:1]([CH:19]1[CH2:33][NH:32][C:31](=O)[CH2:30][N:29](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:28][CH2:27][N:26](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:25][CH2:24][N:23](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:22][C:21](=O)[NH:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C>C1COCC1>[CH2:1]([CH:19]1[CH2:33][NH:32][CH2:31][CH2:30][NH:29][CH2:28][CH2:27][NH:26][CH2:25][CH2:24][NH:23][CH2:22][CH2:21][NH:20]1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 18705600HCID 18705600, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18705601HCID 18705601, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a slurry of 5-octadecyl-1,10,13-tris(p-toluenesulfonyl)-1,4,7,10,13-pentaazacylopentadecane-3,8-dione prepared as in Example 28H (4.00 g, 4.18 mmol) in anhydrous THF (100 ml) under a dry argon atmosphere was added a solution of lithium aluminum hydride in anhydrous THF (105 ml--1.0M, 105 mmol). The resulting solution was refluxed for 40 h. The mixture was quenched by the dropwise addition at 0° C. of H2O (3.25 ml), then 15% NaOH (3.25 ml) and finally H2O (9.60 ml). The resulting slurry was stirred for 1 h, THF (200 ml) was added and the white solid was filtered. The solid was washed with THF (200 ml) and then hot THF (300 ml). The filtrate and washings were combined and the solvent was removed in vacuo. The crude product was purified by recrystallization from THF--ethyl ether and then hexanes to give 1.21 g (62% yield) of the product as a white crystalline solid: mp 99°-100° C.; 1H NMR (CDCl3) δ 0.88 (t, J=6.7 Hz, 3 H), 1.25 (m, 33 H), 1.52 (m, 1 H), 1.66 (br s, 5 H), 2.34 (m, 1 H), 2.72 (m, 18 H); Exact mass (M+H)+ : calcd., 468.5005; found, 468.5034 (C28H62N5).

Workup

  1. temperatureThe resulting solution was refluxed for 40 h
  2. customThe mixture was quenched by the dropwise addition at 0° C. of H2O (3.25 ml)
  3. additionTHF (200 ml) was added
  4. filtrationthe white solid was filtered
  5. washThe solid was washed with THF (200 ml)
  6. customthe solvent was removed in vacuo
  7. customThe crude product was purified by recrystallization from THF

Sources & evidence

ORD record
ord-c892eb5e5b1c4d12b1261f8c3d9f25f1
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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