3-Hydroxybenzaldehyde → Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate

HRID 449503

Reaction equation

HRID 449503 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9](P(OC)(OC)=O)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][C:9](=[CH:24][C:23]1[CH:26]=[CH:27][CH:28]=[C:21]([OH:20])[CH:22]=1)[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 397380Methyl ((tert-butoxy(hydroxy)methylidene)amino)(dimethoxyphosphoryl)acetate

Product 1

HCID 67542936Methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylateYield 96%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyl [(tert-butoxycarbonyl)amino](dimethoxyphosphoryl)acetate (Fluka, Cat. #09659) (0.97 g, 3.3 mmol) and 3-hydroxybenzaldehyde (0.400 g, 3.28 mmol) were combined in methylene chloride (14 mL) at r.t. under nitrogen. To this DBU (0.68 mL, 3.9 mmol) was added and the reaction was stirred at r.t. for 2 h. The reaction was taken up in ethyl acetate, washed with 1 N HCl, brine, dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as an oil. The product was purified by Flash chromatography on a silica gel column eluting hexane: ethyl acetate gradient to give methyl 2-(tert-butoxycarbonylamino)-3-(3-hydroxyphenyl)acrylate (0.92 g, 96%) as a clear oil Analytical LCMS (M+H-Boc)+: m/z=193.9.

Workup

  1. washwashed with 1 N HCl, brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude product as an oil
  5. customThe product was purified by Flash chromatography on a silica gel column
  6. washeluting hexane

Sources & evidence

ORD record
ord-c0676be429e740f2b8ede788a3d1cdd5
Source dataset
uspto-grants-2013_07
Patent number
US08481732B2

Linked notes

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