Potassium ethanethioate → HCID 58665017, compound

HRID 1789666Notes

Reaction equation

HRID 1789666 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].[CH2:6]([O:8][C:9](=[O:38])[C@H:10]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:11][C:12]([C:14]1([NH:19][C:20](=[O:29])[C@H:21](Br)[CH:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[CH3:7]>O1CCCC1.C(OCC)(=O)C>[CH2:6]([O:8][C:9](=[O:38])[C@H:10]([CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[NH:11][C:12]([C:14]1([NH:19][C:20](=[O:29])[C@@H:21]([S:3][C:1](=[O:4])[CH3:2])[CH:22]2[CH2:23][CH2:24][O:25][CH2:26][CH2:27]2)[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[CH3:7]

Participants

5

Reactant 2

HCID 23670855Potassium ethanethioateHCID 69621702HCID 69621702, compound

Product 1

HCID 58665017HCID 58665017, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of potassium thioacetate (1.66 g, 14.6 mmol) and N-[1-[(R)-2-bromo-2-(4-tetrahydropyranyl)acetylamino]-cyclopentanecarbonyl]-L-homophenylalanine ethyl ester (1.84 g, 3.52 mmol) in 50 mL of tetrahydrofuran is stirred at room temperature for 4 hours. The mixture is diluted with ethyl acetate, washed with water, with saturated sodium bicarbonate solution, with brine and then dried over magnesium sulfate. The mixture is filtered and concentrated to dryness in vacuo. The residual oil is chromatographed on silica gel with hexane:ethyl acetate (50:50) to yield the title compound, m.p. 107–111° C.; [αD]−56.27° (c=0.994, methanol).

Workup

  1. washwashed with water, with saturated sodium bicarbonate solution, with brine
  2. dry with materialdried over magnesium sulfate
  3. filtrationThe mixture is filtered
  4. concentrationconcentrated to dryness in vacuo
  5. customThe residual oil is chromatographed on silica gel with hexane:ethyl acetate (50:50)

Sources & evidence

ORD record
ord-c227882dcc304196ab72380614cebcb0
Source dataset
uspto-grants-2006_07
Patent number
US07071169B2

Reaction notes

Loading…