Homovanillic Acid → HCID 178444560, compound

HRID 500080

Reaction equation

HRID 500080 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][C:3]=1[O:12][CH3:13].F[P-](F)(F)(F)(F)F.[N:21]1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2N=N1.ClCCl>C(N(CC)CC)C>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([NH:21][C@H:25]2[CH2:24][CH2:29][C@@H:28](/[CH:7]=[CH:2]/[CH2:3][CH2:4][CH3:5])[CH2:27][CH2:26]2)=[O:11])=[CH:4][C:3]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 1738Homovanillic AcidHCID 6344DichloromethaneHCID 2724699PyBOP

Product 1

HCID 178444560HCID 178444560, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of the above product (2) (2.17 g), 4-hydroxy-3-methoxyphenyacetic acid (1.16 g), benzotriazol-1-yloxy-tris(pyrrolidino)phosphonium hexafluorophosphate (3.33 g) and dichloromethane (50 ml) under ice-cooling was added triethylamine (2.68 ml). The reaction mixture was stirred at room temperature for 1 hour, and then washed with saturated aqueous ammonium chloride and then brine. The organic layer was dried over sodium sulfate, and then the solvent was removed in vacuo. The residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate) and the recrystallized from hexane-ethyl acetate to give 770 mg of the desired compound.

Workup

  1. temperaturecooling
  2. washwashed with saturated aqueous ammonium chloride
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by a silica gel chromatography (eluent: gradient from 100% hexane/0% ethyl acetate to 0% hexane/100% ethyl acetate)
  6. customthe recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-ef16bb072d8446eebb4da8661681bcc3
Source dataset
uspto-grants-2010_08
Patent number
US07767854B2

Linked notes

Loading…