Acetic Acid → 2-{[(Benzyloxy)carbonyl]amino}-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acid

HRID 1759576Notes

Reaction equation

HRID 1759576 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12](O)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.C(O)(=O)C.[O:26]1[CH2:30][CH2:29][C:28]2[CH:31]=[CH:32][CH:33]=[CH:34][C:27]1=2>O>[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:32]1[CH:33]=[CH:34][C:27]2[O:26][CH2:30][CH2:29][C:28]=2[CH:31]=1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 10329DihydrobenzofuranHCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

Product 1

HCID 205312302-{[(Benzyloxy)carbonyl]amino}-2-(2,3-dihydro-1-benzofuran-5-yl)acetic acidYield 35.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-Benzyloxycarbonyl-α-hydroxyglycine (10.4 g., 0.046 mole) was added to a stirred mixture of concentrated sulfuric acid (4 ml.) and glacial acetic acid (36 ml.) at 0°-5° C. followed, after five minutes, by the dropwise addition of 2,3-dihydrobenzo(b)furan (5.8 g., 0.048 mole). The reaction mixture was stirred at ambient temperature overnight and the resulting pale mauve emulsion poured into stirred ice and water to afford a gum, which was induced to solidify. The crude product was collected, washed with water, dried in vacuo, and crystallized from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.) to provide Dl-α-benzyloxycarbonylamino-2,3-dihydro-5-benzo(b)furanyl acetic acid (5.3 g.), m.p. 121°-123° C. Recrystallization of a sample raised the m.p. to 125°-126° C.

Workup

  1. additionthe resulting pale mauve emulsion poured
  2. customto afford a gum, which
  3. customThe crude product was collected
  4. washwashed with water
  5. customdried in vacuo
  6. customcrystallized from a mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-ebaa45d0734c4eafb454c933a1a37765
Source dataset
uspto-grants-1982_07
Patent number
US04341792

Reaction notes

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