HCID 86684667, compound → HCID 71576415, compound

HRID 1504360Notes

Reaction equation

HRID 1504360 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C@H:14]([NH:38]C(=O)OC(C)(C)C)[C:15]([NH:17][C@H:18]2[C@@H:22]([OH:23])[C@H:21]([N:24]3[CH:32]=[N:31][C:30]4[C:25]3=[N:26][CH:27]=[N:28][C:29]=4[N:33]([CH3:35])[CH3:34])[O:20][C@@H:19]2[CH2:36][OH:37])=[O:16])=[CH:9][CH:8]=1)=[N+:2]=[N-:3]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:34][N:33]([C:29]1[C:30]2[N:31]=[CH:32][N:24]([C@@H:21]3[O:20][C@H:19]([CH2:36][OH:37])[C@@H:18]([NH:17][C:15]([C@@H:14]([NH2:38])[CH2:13][C:10]4[CH:11]=[CH:12][C:7]([O:6][CH3:5])=[CH:8][CH:9]=4)=[O:16])[C@H:22]3[OH:23])[C:25]=2[N:26]=[CH:27][N:28]=1)[CH3:35].[NH2:38][C@@H:14]([CH2:13][C:10]1[CH:11]=[CH:12][C:7]([O:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])=[CH:8][CH:9]=1)[C:15]([NH:17][C@H:18]1[C@@H:22]([OH:23])[C@H:21]([N:24]2[CH:32]=[N:31][C:30]3[C:25]2=[N:26][CH:27]=[N:28][C:29]=3[N:33]([CH3:35])[CH3:34])[O:20][C@@H:19]1[CH2:36][OH:37])=[O:16]

Participants

5

Reactant 1

HCID 86684667HCID 86684667, compound

Product 2

HCID 439530PuromycinHCID 71576415HCID 71576415, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Boc-Puromycin analog 4A (392 mg, 0.63 mmol) was dissolved in a 1:1 TFA (5 mL) and CH2Cl2 (5 mL) mixture and then stirred at room temperature for 30 min. Volatiles were evaporated in vacuo and the residue was dissolved into CH2Cl2. The solution was poured into a suspension of saturated aqueous NaHCO3. The organic layer was dried over Na2SO4 and evaporated to dryness in vacuo. The residue was purified by flash chromatography (SiO2, step-wise gradient from 2-15% MeOH in CH2Cl2) to afford Puromycin analog 5A (151 mg, 46%) as a white solid. 1H NMR (600 MHz, DMSO-d6): δ 8.45 (1H, s), 8.24 (1H, s), 8.06 (1H, br), 7.17 (2H, d, J=8.4 Hz), 6.87 (1H, d, J=8.4 Hz), 6.14 (1H, d, J=4.8 Hz), 5.98 (1H, d, J=2.4 Hz), 5.14 (1H, t, J=5.4 Hz), 4.42-4.52 (2H, m), 4.14 (2H, t, J=5.4 Hz), 3.92-3.97 (1H, m), 3.10-3.80 (12H, m), 2.92 (1H, dd, J=13.8, 5.4 Hz), 2.55 (1H, dd, J=13.8, 9.0 Hz), 1.72 (2H, br); 13C NMR (150 MHz, DMSO-d6): δ 174.8, 156.5, 154.3, 151.8, 149.6, 137.9, 131.1, 130.3, 119.6, 114.2, 89.4, 83.6, 79.1, 73.2, 66.7, 61.0, 56.3, 50.0, 49.6, 40.1; MS (ESI, m/z): 527 (M+H)+.

Workup

  1. customVolatiles were evaporated in vacuo
  2. dissolutionthe residue was dissolved into CH2Cl2
  3. additionThe solution was poured into a suspension of saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customThe residue was purified by flash chromatography (SiO2, step-wise gradient from 2-15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-4a7a3d28b73c42a998dd955ba2bdcd11
Source dataset
uspto-grants-2015_12
Patent number
US09212381B2

Reaction notes

Loading…