Ethanol → HCID 71677820, compound

HRID 1527932Notes

Reaction equation

HRID 1527932 reaction equation
[CH:1]1([CH2:7][N:8]2[CH2:12][C@@H:11]([NH:13][C:14]([C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]=3[OH:26])=[O:15])[CH2:10][C@H:9]2[C:27]([OH:29])=[O:28])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[CH2:35](O)[CH3:36]>>[CH2:35]([O:28][C:27]([C@@H:9]1[CH2:10][C@H:11]([NH:13][C:14]([C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]=2[OH:26])=[O:15])[CH2:12][N:8]1[CH2:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:29])[CH3:36]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 89768055HCID 89768055, compound

Product 1

HCID 71677820HCID 71677820, compoundYield 52.3%

Conditions

Temperature
95 °C

Procedure

To a stirred solution of (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid (50 mg, 0.13 mmol) in ethanol (3 mL) was added conc. sulfuric acid (0.1 mL) and the reaction mixture was stirred at 95° C. for 14 h. The reaction mixture was then concentrated under vacuum, diluted with water, extracted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered, concentrated and purified by column chromatography (using 5% EtOAc in hexane as eluent) to give (2S,4S)-1-cyclohexylmethyl-4-[(1-hydroxy-naphthalene-2-carbonyl)-amino]-pyrrolidine-2-carboxylic acid ethyl ester (28 mg, 52.3% yield) as a blue sticky liquid. MS calcd. for C25H33N2O4 [(M+H)+] 425.0, obsd. 425.2.

Workup

  1. concentrationThe reaction mixture was then concentrated under vacuum
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by column chromatography (using 5% EtOAc in hexane as eluent)

Sources & evidence

ORD record
ord-ede5bd8136334b4fbc9114ae1efe3faa
Source dataset
uspto-grants-2015_07
Patent number
US09090559B2

Reaction notes

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