Dichloromethane → HCID 178468201, compound

HRID 1375717Notes

Reaction equation

HRID 1375717 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([O:24][CH2:25][CH3:26])[C:21]([OH:23])=[O:22])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:27]([O:31][C:32]([NH:34][C:35](=[N:38][C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])SC)=[O:33])([CH3:30])([CH3:29])[CH3:28].C(N(CC)C(C)C)(C)C.C(Cl)Cl>C1COCC1.CO.C(Cl)Cl>[C:42]([O:41][C:39]([NH:38][C:35]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][C@H:20]([O:24][CH2:25][CH3:26])[C:21]([OH:23])=[O:22])=[CH:17][CH:18]=2)=[CH:6][CH:7]=1)=[N:34][C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 5466031,3-DI-Boc-2-methylisothioureaHCID 69427755HCID 69427755, compound

Product 1

HCID 178468201HCID 178468201, compoundYield 37.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(2S)-3-{4-[4-(4-Aminophenyl)butoxy]phenyl}-2-ethoxypropanoic acid (140 mg, 0.392 mmol) was dissolved in THF (10 ml). 1,3-Bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (116 mg, 0.392 mmol) was added and then N,N-diisopropylethylamine (126 mg, 0.979 mmol) was added. The mixture was stirred at room temperature for 12 days and thereafter evaporated in vacuum to dryness. Water and ethyl acetate were added into the residue. The mixture was then acidified with 1% hydrochloric acid, pH˜3. The two phases were separated. The water phase was extracted with ethyl acetate (×2). All organic phases were combined and washed with brine and dried with magnesium sulfate. The solvent was evaporated. Chromatography of the residue on an ISOLUTE column (SI, 2 g/6 ml) using DCM and then MeOH/DCM (1:99) as eluant gave an oil. Re-chromatography of the oil on an ISOLUTE column (SI, 2 g/6 ml) using DCM and then MeOH/DCM (0.5:99.5) gave 88 mg desired product, yield 37.5%.

Workup

  1. customevaporated in vacuum to dryness
  2. additionWater and ethyl acetate were added into the residue
  3. customThe two phases were separated
  4. extractionThe water phase was extracted with ethyl acetate (×2)
  5. washwashed with brine
  6. dry with materialdried with magnesium sulfate
  7. customThe solvent was evaporated
  8. customMeOH/DCM (1:99) as eluant gave an oil

Sources & evidence

ORD record
ord-3b7d934abd614a9b942cd708ba9fc5dd
Source dataset
uspto-grants-2007_01
Patent number
US07169810B2

Reaction notes

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