Dichloromethane ethylacetate → HCID 58114115, compound

HRID 1887007Notes

Reaction equation

HRID 1887007 reaction equation
[CH3:1][C:2]([CH3:29])([CH3:28])[C:3]#[C:4][C:5]1[S:9][CH:8]=[C:7]([N:10]([C@H:21]2[CH2:26][CH2:25][C@H:24]([OH:27])[CH2:23][CH2:22]2)[C:11]([C@@H:13]2[C@@H:18]([CH3:19])[CH2:17][C:16]([CH3:20])=[CH:15][CH2:14]2)=[O:12])[CH:6]=1.C(NC(C)C)(C)C.[Li].[C:38]([O:41]CC)(=[O:40])C.ClCCl>C1COCC1>[CH3:29][C:2]([CH3:28])([CH3:1])[C:3]#[C:4][C:5]1[S:9][C:8]([C:38]([OH:41])=[O:40])=[C:7]([N:10]([C:11]([C@@H:13]2[C@@H:18]([CH3:19])[CH2:17][C:16]([CH3:20])=[CH:15][CH2:14]2)=[O:12])[CH:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)[CH:6]=1

Participants

5

Reactant 3

HCID 21226138Dichloromethane ethylacetateHCID 45051747Lithium diisopropylamineHCID 178426069HCID 178426069, compound

Product 1

HCID 58114115HCID 58114115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

(1S,6S)-4,6-Dimethyl-cyclohex-3-ene-carboxylic acid [5-(3,3-dimethyl-but-1-ynyl)-thiophen-3-yl]-(trans-4-hydroxy-cyclohexyl)-amide (1.74 g, 4.2 mmol) in THF (50 mL) was cooled to −78° C. and treated with lithium diisopropylamine (8.4 mL, 2.0M in heptane/THF/PhEt, 16.8 mmol) and allowed to warm to 0° C. over the course of 2 hours. CO2 was vigorously bubbled through the reaction solution for 10 minutes. The reaction was then quenched with the addition of iPrOH, diluted with ethyl acetate, washed with saturated NH4Cl(aq), dried over MgSO4, filtered, and concentrated. Silica gel chromatography (0-100% ethyl acetate/dichloromethane) afforded 530 mg (1.2 mmol) of the title compound: MS (m/z): 458.1 [M+H]+; HPLC retention time 4.35 min (2-98% acetonitrile: water with 0.05% trifluoroacetic acid).

Workup

  1. customCO2 was vigorously bubbled through the reaction solution for 10 minutes
  2. customThe reaction was then quenched with the addition of iPrOH
  3. additiondiluted with ethyl acetate
  4. washwashed with saturated NH4Cl(aq)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-36a4caa9428045f5a5e505f29db92de0
Source dataset
uspto-grants-2013_08
Patent number
US08501714B2

Reaction notes

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