Diethyl Ether → HCID 86675383, compound

HRID 1523109Notes

Reaction equation

HRID 1523109 reaction equation
C([O:8][C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:26][C:27]([O:29]CC2C=CC=CC=2)=[O:28])[CH2:18][CH2:17][CH2:16][N:15]([CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][C:42]([N+:45]([O-])=O)=[CH:41][CH:40]=2)[CH2:14][CH2:13]1)=[O:10])C1C=CC=CC=1.CCOCC>C(O)C.[Pd]>[C:9]([CH2:11][N:12]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20][N:19]([CH2:26][C:27]([OH:29])=[O:28])[CH2:18][CH2:17][CH2:16][N:15]([CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([NH2:45])=[CH:43][CH:44]=2)[CH2:14][CH2:13]1)([OH:10])=[O:8]

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 71133769HCID 71133769, compound

Product 1

HCID 86675383HCID 86675383, compoundYield 98.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of compound (16) (0.86 g, 1.33 mmol) in absolute ethanol (100 ml) was added 10% Pd/C (0.26 g). The resultant mixture was stirred at an ambient temperature under H2 atmosphere for 12 hours. The reaction mixture was filtered through a celite pad and washed with ethanol (2×20 ml). The solvent was evaporated from the combined filtrate in vacuo to give an oily residue, which was then treated with Et2O to obtain a white solid of compound (12) (0.57 g, 98% yield). 1H NMR (500 MHz, D2O): δ 7.45-7.43 (dd, 2H), 7.38-7.36 (dd, 2H), 3.49-3.12 (m, 18H), 2.82-2.62 (m, 6H), 1.91 (brs, 4H); 13C NMR (125 MHz, D2O): δ 177.0, 176.6, 163.4, 163.1, 162.8, 162.5, 137.4, 130.4, 128.9, 123.4, 119.9, 117.5, 115.2, 112.9, 56.0, 54.9, 54.4, 53.3, 51.6, 50.5, 48.8, 47.3, 45.0, 31.5, 27.6, 22.8, 21.3; FIRMS (FAB) calculated for C22H38N5O4: 436.2924 [(M+H)+], measured value: 436.2925 [(M+H)+].

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washwashed with ethanol (2×20 ml)
  3. customThe solvent was evaporated from the combined filtrate in vacuo
  4. customto give an oily residue, which

Sources & evidence

ORD record
ord-a8c7b940754742bdaff5824b277c3dd0
Source dataset
uspto-grants-2015_07
Patent number
US09079867B2

Reaction notes

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