1,2-Dichloroethane → HCID 9138898, compound

HRID 2239601Notes

Reaction equation

HRID 2239601 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21](O)=[O:22])=[O:16])([CH3:13])([CH3:12])[CH3:11].C(Cl)CCl>C1COCC1.CN(C1C=CN=CC=1)C>[C:10]([O:14][C:15]([NH:17][CH2:18][CH2:19][CH2:20][C:21]([O:9][C:3]1[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])=[O:22])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 113352,6-DimethylphenolHCID 2948944-(((Tert-butoxy)carbonyl)amino)butanoic acid

Product 1

HCID 9138898HCID 9138898, compoundYield 76.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
1 °C

Procedure

2,6-Dimethylphenol (0.257 g, 2.1 mmol) and 4-[(tert-butoxycarbonyl)amino]butanoic acid (0.427 g, 2.1 mmol) were dissolved in THF (10 ml, dry) and DMAP (0.005 g, 0.04 mmol) was added. After cooling down to 0-2° C., EDC (0.483 g, 2.52 mmol) was added portionwise under nitrogen atmosphere. The ice bath was removed and stirring was continued over night at rt. After 17 h, the mixture was diluted with DCM (50 ml) and extracted with water (20 ml), HCl (2N, 20 ml) and water (20 ml) again. The organic layer was dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel, using DCM/MeOH (95:5) as eluent, to give the title compound (0.493 g, 76%) as a colorless solid. 1H NMR (400 MHz, CDCl3): δ 1.45 (s 9H), 1.94-2.01 (m, 2H), 2.14 (s, 6H), 2.66 (t, 2H), 3.24-3.29 (m, 2H), 4.66 (bs, 1H), 7.05 (s, 3H); Mass Spectrum: M-tert-Bu+H+ 252.1

Workup

  1. customThe ice bath was removed
  2. waitwas continued over night at rt
  3. additionthe mixture was diluted with DCM (50 ml)
  4. extractionextracted with water (20 ml), HCl (2N, 20 ml) and water (20 ml) again
  5. dry with materialThe organic layer was dried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e825625a6fe14427bd643f39a07070c6
Source dataset
uspto-grants-2010_05
Patent number
US07723333B2

Reaction notes

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