Formaldehyde → HCID 67248586, compound

HRID 1035316Notes

Reaction equation

HRID 1035316 reaction equation
[CH3:1][C:2]1[C:12]2[O:11][CH2:10][CH2:9][C@H:8]3[CH2:13][NH:14][CH2:15][CH2:16][N:7]3[C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:17]=O>>[CH3:17][N:14]1[CH2:15][CH2:16][N:7]2[C@@H:8]([CH2:9][CH2:10][O:11][C:12]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=32)[CH2:13]1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 67248740HCID 67248740, compound

Product 1

HCID 67248586HCID 67248586, compound

Procedure

To a solution of Example 226 (50 mg, 0.229 mmol) in a pH 4 buffer solution (10 mL, made from 48 g acetic acid and 30.5 g sodium acetate in 1 L methanol) was added formaldehyde (36% solution, 13.8 mg, 0.46 mmol) and macroporous-cyanoborohydride resin (0.32 g, 0.69 mmol). The reaction was allowed to stir for 2 hours before the macroporous-cyanoborohydride resin was removed by filtration, and the solution concentrated. The concentrate was basified to pH=10 with NaOH (1 M aqueous), and the product was extracted with ethyl acetate. Purification via flash chromatography (0-30% methanol/dichloromethane) afforded the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.69-6.86 (m, 3H), 4.24-4.37 (m, 1H), 4.06-4.16 (m, 1H), 2.99-3.18 (m, 3H), 2.56-2.68 (m, 1H), 2.46-2.55 (m, 1H), 2.18-2.29 (m, 1H), 2.21 (s, 3H), 2.02-2.16 (m, 1H), 2.09 (s, 3H), 1.79-1.99 (m, 2H); MS (DCI+) m/z 233 (M+H)+.

Workup

  1. customwas removed by filtration
  2. concentrationthe solution concentrated
  3. extractionthe product was extracted with ethyl acetate
  4. customPurification via flash chromatography (0-30% methanol/dichloromethane)

Sources & evidence

ORD record
ord-55faa36fee064021a0c1fee8ab49d4b2
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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