Acetic Acid → HCID 13505683, compound

HRID 464567Notes

Reaction equation

HRID 464567 reaction equation
[Br:1][C@@H:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[C:15]1([C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N+]=[N-])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)(=O)C>CC(C)=O>[Br:1][C@@H:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]([O:5][CH:21]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 612301,1'-(Diazomethylene)bis(benzene)HCID 12961659Propanoic acid, 2-bromo-3-(phenylmethoxy)-, (S)-

Product 1

HCID 13505683HCID 13505683, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of (S)-2-bromo-3-(phenylmethoxy)propanoic acid (7.63 g, 29.4 mmol) in acetone (30 ml) was added solid diphenyldiazomethane (5.81 g, 29.9 mmol) over the course of three minutes. The solution heated and nitrogen evolved vigorously. The purple solution was stirred for an additional 45 minutes, followed by the addition of acetic acid (1 ml) to quench any residual diphenyldiazomethane. The solution was extracted with saturated sodium bicarbonate (50 ml), washed with saturated sodium chloride (50 ml), dried over magnesium sulfate and evaporated at reduced pressure to give the crude product (11.24 g). Purification by chromatography on silica gel (95:5; hexane:ethyl acetate) afforded the title compound (6.38 g).

Workup

  1. temperatureThe solution heated
  2. customto quench any residual diphenyldiazomethane
  3. extractionThe solution was extracted with saturated sodium bicarbonate (50 ml)
  4. washwashed with saturated sodium chloride (50 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated at reduced pressure
  7. customto give the crude product (11.24 g)
  8. customPurification by chromatography on silica gel (95:5; hexane:ethyl acetate)

Sources & evidence

ORD record
ord-2227aa94be1a4698b61d845789be9ba1
Source dataset
uspto-grants-1985_10
Patent number
US04548751

Reaction notes

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