Ethanol → HCID 13575046, compound

HRID 235915Notes

Reaction equation

HRID 235915 reaction equation
[O:1]=[C:2]([NH:13][C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([O:22]CC1C=CC=CC=1)=[O:21])=[O:17])[CH3:15])[CH2:3][CH2:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.CO.C(O)C.[OH-].[Na+]>O>[O:1]=[C:2]([NH:13][C@H:14]([C:16]([N:18]1[CH2:32][CH2:31][CH2:30][C@H:19]1[C:20]([OH:22])=[O:21])=[O:17])[CH3:15])[CH2:3][CH2:4][C:5](=[O:12])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 14798Sodium HydroxideHCID 131714102HCID 131714102, compound

Product 1

HCID 13575046HCID 13575046, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the phenylmethyl ester product from part (a) (1.3 g., 3.0 mmole), methanol (3.5 ml.), ethanol (3.5 ml.), water (3.5 ml.), and 1N aqueous sodium hydroxide solution (3.5 ml., 3.5 mmole) is stirred at 25° for 17 hours, after which it is partially concentrated by rotary evaporation (to remove volatile alcohols). The solution is then diluted with water and washed with ethyl acetate (the ethyl acetate layer is discarded). The aqueous layer is acidified with hydrochloric acid and extracted twice with ethyl acetate. The extracts are combined, dried, and concentrated to give 1.0 g. of the desired product as a pale yellow oil. This oil is dissolved in water (150 ml.), filtered through charcoal, and lyophilized to give 500 mg. of 1-[N-(1,4-dioxo-4-phenylbutyl)-L-alanyl]-L-proline as a fluffy white powder. TLC (Rf 0.4 on silica gel, 1:1 methanol:ethyl acetate). [α]D =-80° (1% chloroform).

Workup

  1. concentrationafter which it is partially concentrated by rotary evaporation (to remove volatile alcohols)
  2. additionThe solution is then diluted with water
  3. washwashed with ethyl acetate (the ethyl acetate layer
  4. extractionextracted twice with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customto give 1.0 g

Sources & evidence

ORD record
ord-b6b9b998f8b0415b9a2d4d371faadfc1
Source dataset
uspto-grants-1987_02
Patent number
US04642315

Reaction notes

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