Acetic Acid → HCID 22093835, compound

HRID 2229525Notes

Reaction equation

HRID 2229525 reaction equation
[O:1]([C:8]1[CH:13]=[CH:12][C:11]([C:14]([NH:16][CH:17]([CH2:21][CH2:22][CH3:23])[C:18]([OH:20])=O)=[O:15])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Na].[H][H].C(O)(=[O:36])C.[O:38]1[CH2:42]C[CH2:40][CH2:39]1>>[CH2:39]([O:38][CH2:42][O:20][CH2:18][C@@H:17]([NH:16][C:14]([C:11]1[CH:10]=[CH:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:13][CH:12]=1)=[O:15])[CH2:21][CH2:22][CH2:23][OH:36])[CH3:40]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86758363HCID 86758363, compoundHCID 178506446HCID 178506446, compound

Product 1

HCID 22093835HCID 22093835, compound

Conditions

Temperature
0 °C

Procedure

5-Ethoxymethoxy-4(S)-(N-(4-phenoxyphenylcarbonyl)aminopentanoic acid was obtained by the same procedure as a series of reaction of Example 37→Example 39→Example 41→Example 42, using a corresponding compound instead of the compound of a series of Reference Example 4. A solution of the above obtained compound (3.62 g) in tetrahydrofuran (100 ml) was cooled to 0° C. Triethylamine (1.69 ml) and ethylchloro formate (1.2 ml) were added dropwise thereto. The mixture was stirred at 0° C. for 1.5 hours. Sodium hydrogen borone (0.5 equivalent) was added to the reaction mixture. The mixture was stirred for 30 minutes. Acetic acid (5 ml) was added dropwise thereto. The mixture was stirred for 30 minutes and concentrated. To the residue, ethyl acetate and water were added. The organic layer was collected, washed with water and an aqueous saturated solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (Ethyl acetate:Hexane=2:1 (containing 1% triethylamine.)→4:1) to give the title compound (1.84 g) having the following physical data.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. stirringThe mixture was stirred for 30 minutes
  3. concentrationconcentrated
  4. additionTo the residue, ethyl acetate and water were added
  5. customThe organic layer was collected
  6. washwashed with water
  7. dry with materialan aqueous saturated solution of sodium chloride, dried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (Ethyl acetate
  10. additionHexane=2:1 (containing 1% triethylamine.)→4:1)

Sources & evidence

ORD record
ord-becf7e7249fd4b4d820e4e8f27417004
Source dataset
uspto-grants-2002_07
Patent number
US06420427B1

Reaction notes

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