HCID 102526944, compound → Pactamycin

HRID 1056864Notes

Reaction equation

HRID 1056864 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([NH:10][C@@H:11]2[C@@:15]([CH2:17][O:18][C:19](=[O:28])[C:20]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:21]=3[OH:27])([OH:16])[C@@:14]([OH:30])([CH3:29])[C@:13]([NH:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])([C@@H:31]([OH:33])[CH3:32])[C@H:12]2[NH:40]C(OCC2C=CC=CC=2)=O)[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:2]>[OH-].[OH-].[Pd+2].CO>[CH3:26][C:25]1[C:20]([C:19]([O:18][CH2:17][C@:15]2([OH:16])[C@@:14]([OH:30])([CH3:29])[C@:13]([NH:34][C:35]([N:37]([CH3:39])[CH3:38])=[O:36])([C@@H:31]([OH:33])[CH3:32])[C@@H:12]([NH2:40])[C@@H:11]2[NH:10][C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([C:1]([CH3:2])=[O:3])[CH:5]=2)=[O:28])=[C:21]([OH:27])[CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 102526944HCID 102526944, compound

Product 1

HCID 5289124PactamycinYield 89.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A 4-mL vial was charged with salicylate 16 (0.0075 g, 0.01 mmol, 1.0 equiv), and Pd(OH)2/C (20 wt. %, 0.005 g). MeOH (1 mL) was added and the vial was sealed with a Teflon cap. The atmosphere was replaced by H2 (balloon, ˜1 atm.) and stirred until TLC analysis indicated complete consumption of the starting material, typically 20 min. The resulting suspension was filtered through a pad of CELITE® 545 (diatomaceous earth, filter aid) and washed with MeOH. The homogeneous solution was concentrated in vacuo. The crude residue was purified by flash chromatography (98:2 CH2Cl2:MeOH) affording pactamycin (0.005 g, 82%) as a pale yellow solid. Analytical data: [α]D19+27.4 (c=0.40, CHCl3); 1H NMR (600 MHz, CDCl3): δ 10.98 Or s, 1H), 7.91 (d, J=10.8 Hz, 1H), 7.26-7.23 (m, 4H), 7.18-7.16 (m, 2H), 6.81-6.78 (m, 2H), 6.64 (d, J=7.2 Hz, 1H), 5.78 (br s, 1H), 5.67 (d, J=10.8 Hz, 1H), 4.84 and 4.79 (ABq, J=12.6 Hz, 2H), 3.93 (m, 1H), 3.80 (d, J=10.2 Hz, 1H), 2.99 (s, 6H), 2.95 (s, 1H), 2.55 (s, 3H), 2.38 (s, 3H), 1.55 (s, 3H), 1.04 (d, J=6.0 Hz, 3H); 13C NMR (150 MHz, CDCl3): δ 198.5, 172.6, 162.8, 159.2, 146.6, 141.2, 138.3, 134.6, 129.6, 123.0, 118.7, 118.4, 115.7, 112.0, 110.8, 88.8, 84.9, 74.3, 71.5, 68.7, 65.4, 63.2, 36.9, 29.7, 26.7, 24.1, 21.1, 18.1; HRMS (ESI1) Calcd. for C28H38N4O8+H, 559.2762. Found, 559.2763. IR (thin film, cm−1) 3393, 2938, 2359, 2341, 1698, 1652, 1520, 1473, 1418, 1338, 873, 668; TLC (95:5 CH2Cl2/MeOH): Rf=0.30.

Workup

  1. customcap
  2. customconsumption of the starting material, typically 20 min
  3. filtrationThe resulting suspension was filtered through a pad of CELITE® 545 (diatomaceous earth, filter aid)
  4. washwashed with MeOH
  5. concentrationThe homogeneous solution was concentrated in vacuo
  6. customThe crude residue was purified by flash chromatography (98:2 CH2Cl2:MeOH)

Sources & evidence

ORD record
ord-e57b9230244f481c99b0ba1259bee486
Source dataset
uspto-grants-2016_07
Patent number
US09399652B2

Reaction notes

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