Formaldehyde → HCID 178499253, compound

HRID 2099661Notes

Reaction equation

HRID 2099661 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:25])=[CH:8][C:9]=1[N:10]([CH:20]([CH2:23][OH:24])[CH2:21][OH:22])[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4].C=O.[C:28]([O-])(O)=O.[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([Br:25])=[CH:8][C:9]=1[N:10]([CH:20]1[CH2:23][O:24][CH2:28][O:22][CH2:21]1)[C:11]([C@H:13]1[CH2:18][CH2:17][C@H:16]([CH3:19])[CH2:15][CH2:14]1)=[O:12])=[O:4]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 178499254HCID 178499254, compound

Product 1

HCID 178499253HCID 178499253, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-3-[(2-hydroxy-1-hydroxymethyl-ethyl)-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (18 mg, 0.041 mmol), paraformaldehyde (6 mg) and boron trifluoride-diethyl etherate (15 μl, 0.12 mmol) in dry dioxane (0.6 mL) was stirred at 80° C. for 14 min. It was cooled and added to ice and NaHCO3 solution mixture, extracted with ethyl acetate, washed with brine, dried and evaporated. Pure 5-bromo-3-[[1,3]dioxan-5-yl-(trans-4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester was obtained after chromatography over silica gel (hexane:ethyl acetate—9:1 as eluent) (15 mg; 81%).

Workup

  1. temperatureIt was cooled
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-6c01eec6571044e5b8b2533632c4c491
Source dataset
uspto-grants-2009_08
Patent number
US07569600B2

Reaction notes

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