Methanol → HCID 46195744, compound

HRID 710492Notes

Reaction equation

HRID 710492 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][N:22]4[CH:27]3[CH2:32][O:31]C(C)(C)[O:29][CH2:28]3)[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[Na+].[I-].CO>CC#N>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:26]=[CH:25][CH:24]=[C:23]4[C:19]=3[CH2:20][CH2:21][N:22]4[CH:27]([CH2:32][OH:31])[CH2:28][OH:29])[N:14]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 5238Sodium IodideHCID 66726559HCID 66726559, compound

Product 1

HCID 46195744HCID 46195744, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of the product of Step A (0.0346 g; 0.0743 mmol) and NaI (0.033 g; 0.22 mmol) in anhydrous CH3CN (1 ml) Me3SiCl (0.1 ml) was added at room temperature under N2. After stirring for 30 min at room temperature MeOH (2 ml) was added and the resulting mixture was evaporated to dryness under reduced pressure. The residue was partitioned between EtOAc (5 ml) and 1% NaHCO3 (5 ml). The precipitate formed was filtered off, washed with H2O (5 ml), fresh EtOAc (5 ml) and dried to give the title compound (0.019 g; 61%) as creamy solid. 1H-NMR (DMSO-d6) 1.28-1.41 (m, 6H): 3.2-3.4 (m, 2H+H2O); 3.5-4.02 (m, 7H); 4.07-4.18 (m, 4H); 4.6 (broad s, 2H); 6.52 (d, 1H, J=6 Hz); 7.06-7.19 (m, 3H); 7.58 (d, 1H, J=3 Hz); 7.72 (dd, 1H, J=9 Hz).

Workup

  1. additionwas added
  2. customthe resulting mixture was evaporated to dryness under reduced pressure
  3. customThe residue was partitioned between EtOAc (5 ml) and 1% NaHCO3 (5 ml)
  4. customThe precipitate formed
  5. filtrationwas filtered off
  6. washwashed with H2O (5 ml), fresh EtOAc (5 ml)
  7. customdried

Sources & evidence

ORD record
ord-310346c53c6745c485942444949a26ac
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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