Formaldehyde → HCID 131727928, compound

HRID 2242665Notes

Reaction equation

HRID 2242665 reaction equation
F[C:2](F)(F)C([O-])=O.[CH2:8]([NH2+:15][CH:16]1[CH2:21][CH2:20][CH:19]([C@H:22]([CH3:40])[C@H:23]([NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[C:24]([N:26]2[CH2:30][CH2:29][C@H:28]([F:31])[CH2:27]2)=[O:25])[CH2:18][CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.C(OCC)(=O)C>[C:36]([O:35][C:33](=[O:34])[NH:32][C@H:23]([C:24]([N:26]1[CH2:30][CH2:29][C@H:28]([F:31])[CH2:27]1)=[O:25])[C@H:22]([CH:19]1[CH2:20][CH2:21][CH:16]([N:15]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:2])[CH2:17][CH2:18]1)[CH3:40])([CH3:39])([CH3:38])[CH3:37]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 87453432HCID 87453432, compound

Product 1

HCID 131727928HCID 131727928, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the material prepared in Step A (0.25 g, 0.54 mmol) in methanol (6 mL) was added a 37% aqueous solution of formaldehyde (0.10 mL, 1.62 mmol), followed by sodium triacetoxyborohydride (0.46 g, 2.16 mmol). After 3 h at ambient temperature the reaction was diluted with 100 mL of ethyl acetate, and the organic layer was washed with saturated aqueous sodium bicarbonate and brine, dried (magnesium sulfate) and concentrated in vacuo, affording the title compound as a clear oil. This material was used without further purification. LC/MS 476.5 (M+1).

Workup

  1. washthe organic layer was washed with saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried (magnesium sulfate)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-41857a533db04858ac09836346bd3ca9
Source dataset
uspto-grants-2010_03
Patent number
US07671073B2

Reaction notes

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