Acetic Acid → HCID 22615044, compound

HRID 843136Notes

Reaction equation

HRID 843136 reaction equation
[CH2:1]([O:3][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[O:17][C:18]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][NH:30][CH2:31][C:32]5[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=5)[C:19]=4[C:20]=3[CH3:21])=[CH:10][C:8]=2[CH:9]=1)[CH3:2].C=O.[C:40](O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH2:1]([O:3][CH2:4][C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C:16]3[O:17][C:18]4[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][CH2:28][CH2:29][N:30]([CH3:40])[CH2:31][C:32]5[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=5)[C:19]=4[C:20]=3[CH3:21])=[CH:10][C:8]=2[CH:9]=1)[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 22614951HCID 22614951, compound

Product 1

HCID 22615044HCID 22615044, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of the compound of Example 42 (25.3 mg), formalin (37%, 5.7 μl), acetic acid (12 μl) and sodium cyanoborohydride (6.4 mg) was stirred in MeOH (2 ml) at room temperature for 1.5 hours. MeOH was evaporated to dryness, the residue was purified by silica gel TLC (dichloromethane-MeOH=10:1) to give the title compound as a colorless oil (23.4 mg). FAB-MS: m/z 515 (MH+); 1H-NMR (CDCl3): δ 1.26 (3H, t, J=7 Hz), 2.03 (2H, quintet, J=6.5 Hz), 2.25 (3H, s), 2.27 (3H, s), 2.61 (2H, t, J=7 Hz), 3.55 (2H, s), 3.61 (2H, q, J=7 Hz), 4.10 (2H, t, J=6 Hz), 4.57 (2H, s), 5.09 (2H, s), 6.58 (1H, d, J=8 Hz), 6.63 (1H, s), 6.97 (1H, dd, J=9 Hz, 2.5 Hz), 7.0-7.2 (4H, m), 7.37 (1H, d, J=9 Hz), 7.64 (1H, dt, 7.5 Hz, 1.5 Hz), 8.42 (1H, dd, J=5 Hz, 1.5 Hz), 8.51 (1H, d, J=1.5 Hz).

Workup

  1. customMeOH was evaporated to dryness
  2. customthe residue was purified by silica gel TLC (dichloromethane-MeOH=10:1)

Sources & evidence

ORD record
ord-59e56b6b1e5c43eea93649d552d65bb4
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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