Diethyl Ether → HCID 13785503, compound

HRID 1905776Notes

Reaction equation

HRID 1905776 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([C:11]([OH:13])=[O:12])[NH2:10])[CH:5]=[CH:6][C:7]=1[OH:8].O.C1(C)C(S(O)(=O)=O)=CC=CC=1.[C:26]1([C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[N+]=[N-])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.CCOCC>CN(C)C=O>[OH:1][C:2]1[CH:3]=[C:4]([CH:9]([C:11]([O:13][CH:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[O:12])[NH2:10])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 279152-Amino-2-(3,4-dihydroxyphenyl)acetic acidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 124969952-Methylbenzenesulfonic acid hydrate

Product 1

HCID 13785503HCID 13785503, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Into a stirred suspension of 1.83 g (10.0 mmol) of α-(3,4-dihydroxyphenyl)glycine and 1.96 g (10.0 mmol) of toluenesulfonic acid monohydrate (97%) in 5 ml of dry dimethylformamide, a solution of freshly prepared diphenyldiazomethane (2.91 g, 15.0 mmoles) in 10 ml of dimethylformamide was dropped at 50° C. and stirring was continued for 10 minutes. The solvent was evaporated in vacuo, the residue was taken up in ice water/ethyl acetate and the pH was brought to 7.5 by addition of dilute sodium hydroxide. The organic layer was separated, washed with sodium bicarbonate solution and brine, dried (sodium sulfate) and evaporated in vacuo to leave a solid which was stirred with ether. Yield (after filtration and drying in vacuo): 1.89 g, melting point 155°-158° C.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe pH was brought to 7.5 by addition of dilute sodium hydroxide
  3. customThe organic layer was separated
  4. washwashed with sodium bicarbonate solution and brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated in vacuo
  7. customto leave a solid which
  8. customYield
  9. filtration(after filtration and drying in vacuo)

Sources & evidence

ORD record
ord-5173ea2911504eb6997f575b27bd93f0
Source dataset
uspto-grants-1987_03
Patent number
US04647660

Reaction notes

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