Hydrochloric Acid → HCID 23630722, compound

HRID 1929299Notes

Reaction equation

HRID 1929299 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[C:12]2[N:13]=[CH:14][N:15]([C:31]=2[N:32]=[C:33]([NH:35]C(=O)COC2C=CC=CC=2)[N:34]=1)[C@@H:16]1[O:30][C@H:27]([CH2:28][OH:29])[C@@H:18]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:17]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O.Cl>CC#N>[CH2:3]([O:10][C:11]1[C:12]2[N:13]=[CH:14][N:15]([C:31]=2[N:32]=[C:33]([NH2:35])[N:34]=1)[C@@H:16]1[O:30][C@H:27]([CH2:28][OH:29])[C@@H:18]([O:19][Si:20]([C:23]([CH3:24])([CH3:26])[CH3:25])([CH3:22])[CH3:21])[CH2:17]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 23630517HCID 23630517, compound

Product 1

HCID 23630722HCID 23630722, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

NaOH (2 M, 21 mL, 42.3 mmol) is added to a solution of 9 (2.56 g, 4.23 mmol) dissolved in CH3CN (13 mL) and stirred at room temperature for 21 h. Water (20 mL) is added to the reaction and the pH is adjusted to 7 with HCl. The solution is extracted with CH2Cl2 (2×30 mL), and the organic extracts are combined, dried over MgSO4, and filtered. The solvent is removed under reduced pressure to yield 10 as a white solid (1.86 g, 93.4%). 1H NMR (DMSO-d6) δ 8.11 (1H, s, H-8), 7.51-7.48 (2H, m, Bn Ar), 7.42-7.33 (3H, m, Bn Ar), 6.50 (211, br s, N2H2, exchanges with D2O), 6.21 (1H, dd, J=8.0, J=6.0, 11-1′), 5.50 (2H, s, CH2-Ph), 5.04 (1H, t, J=5.6, 5′-OH, exchanges with D2O), 4.53 (1H, ddd, J=5.2, J=2.4, J=2.4, H-3′), 3.82 (1H, ddd, J=4.4, J=4.4, J=2.4, H-4′), 3.55 (H-1, ddd, J=11.6, J=5.2, J=5.2, H-5′), 3.49 (1H, ddd, J=11.6, J=5.2, J=4.8, H-5′), 2.70 (1H, ddd, J=13.2, J=8.0, J=5.6, H-2′), 2.21 (1H, ddd, J=12.8, J=5.6, J=2.4, H-2′), 0.90 (9H, s, Si—C(CH3)3), 0.11 (6H, s, Si—(CH3)2). Anal. (C23H33N5O4Si) C, H, N.

Workup

  1. extractionThe solution is extracted with CH2Cl2 (2×30 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-8f0c47482b844d63a9ce0b05876040f3
Source dataset
uspto-grants-2012_05
Patent number
US08188055B2

Reaction notes

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