HCID 86684663, compound → HCID 71576433, compound

HRID 1504356Notes

Reaction equation

HRID 1504356 reaction equation
[CH3:1][N:2]([CH3:43])[C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C@@H:12]1[O:16][C@H:15]([CH2:17][OH:18])[C@@H:14]([NH:19][C:20](=[O:41])[C@@H:21]([NH:33]C(=O)OC(C)(C)C)[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[CH:32])=[CH:25][CH:24]=2)[C@H:13]1[OH:42]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:33][C@@H:21]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]#[CH:32])=[CH:25][CH:24]=1)[C:20]([NH:19][C@H:14]1[C@@H:13]([OH:42])[C@H:12]([N:7]2[CH:6]=[N:5][C:4]3[C:8]2=[N:9][CH:10]=[N:11][C:3]=3[N:2]([CH3:43])[CH3:1])[O:16][C@@H:15]1[CH2:17][OH:18])=[O:41]

Participants

4

Reactant 1

HCID 86684663HCID 86684663, compound

Product 1

HCID 71576433HCID 71576433, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

O-Propargyl Boc-Puromycin 4 (480 mg, 0.81 mmol) was dissolved in a 1:1 TFA (4 mL) and CH2Cl2 (4 mL) mixture and then stirred at room temperature for 30 min. Volatiles were evaporated in vacuo and the residue was dissolved in CH2Cl2. The solution was poured into 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 5-15% MeOH in CH2Cl2) to afford the O-propargyl-puromycin 5 (111 mg, 28%) as a white solid. 1H NMR (600 MHz, DMSO-d6): δ 8.44 (s, 1H), 8.24 (s, 1H), 8.06 (br, 1H), 7.17 (d, J=8.4 Hz, 2H), 6.90 (d, J=8.4 Hz, 2H), 6.13 (d, J=5.4 Hz, 1H), 5.98 (d, J=3.0 Hz, 1H), 5.13 (t, J=5.4 Hz, 1H), 4.74 (d, J=1.8 Hz, 2H), 4.42-4.51 (m, 2H), 3.91-3.96 (m, 1H), 3.66-3.72 (m, 1H), 3.26-3.58 (m, 9H), 2.92 (dd, J=14.4, 4.8 Hz, 1H), 2.52-2.58 (m, 1H), 2.02 (br, 2H); 13C NMR (150 MHz, DMSO-d6): δ 174.6, 155.7, 154.3, 151.8, 149.6, 137.9, 131.3, 130.2, 119.6, 114.5, 89.4, 83.5, 79.4, 78.0, 73.2, 61.0, 56.1, 55.3, 50.0, 40.4, 40.0; HRMS: (ESI, m/z) calcd [M+H]+ for C24H29N7O5: 496.2303. found 496.2308.

Workup

  1. customVolatiles were evaporated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. additionThe solution was poured into 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 5-15% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-b72bd5cb3d22429b88debdf61d6204b8
Source dataset
uspto-grants-2015_12
Patent number
US09212381B2

Reaction notes

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