Formaldehyde → HCID 58617415, compound

HRID 2223151Notes

Reaction equation

HRID 2223151 reaction equation
[CH:1]1([NH:5][CH:6]([CH3:46])[CH2:7][CH2:8][N:9]([C@@H:24]([C:26]2[N:27]([C:37]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH3:45])=[CH:39][CH:38]=3)[C:28](=[O:36])[C:29]3[CH:35]=[CH:34][CH:33]=[N:32][C:30]=3[N:31]=2)[CH3:25])[C:10](=[O:23])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)[CH2:4][CH2:3][CH2:2]1.C=O.[C:49](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[CH:1]1([N:5]([CH3:49])[CH:6]([CH3:46])[CH2:7][CH2:8][N:9]([C@@H:24]([C:26]2[N:27]([C:37]3[CH:38]=[CH:39][C:40]([O:43][CH2:44][CH3:45])=[CH:41][CH:42]=3)[C:28](=[O:36])[C:29]3[CH:35]=[CH:34][CH:33]=[N:32][C:30]=3[N:31]=2)[CH3:25])[C:10](=[O:23])[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([C:19]([F:21])([F:20])[F:22])[CH:13]=2)[CH2:2][CH2:3][CH2:4]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58617393HCID 58617393, compound

Product 1

HCID 58617415HCID 58617415, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

E4 (31 mg, 0.048 mmol), formaldehyde (37% in water, 5.4 μL, 0.073 mmol), and sodium triacetoxyborohydride (31 mg, 0.15 mmol) was stirred in dichloroethane at room temperature for 45 min. The reaction mixture was diluted with dichloromethane, then washed with saturated aqueous sodium bicarbonate and brine. It was dried over magnesium sulfate, filtered, and concentrated in vacuo. 33 mg of E5 was recovered.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialIt was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. custom33 mg of E5 was recovered

Sources & evidence

ORD record
ord-435b0763eee8412d9108cde9bb9607b4
Source dataset
uspto-grants-2008_05
Patent number
US07375102B2

Reaction notes

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