Potassium Carbonate → HCID 11370462, compound

HRID 1169883Notes

Reaction equation

HRID 1169883 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[OH:16])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:25][C:26]([NH2:28])=[O:27]>CN(C=O)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[O:16][CH2:25][C:26](=[O:27])[NH2:28])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 11311441N-t-Butoxycarbonyl-2-Hydroxy-5-Chlorobenzylamine

Product 1

HCID 11370462HCID 11370462, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloro-2-hydroxy-benzyl)-carbamic acid tert-butyl ester 78 (210 mg, 0.8 mmol) was dissolved in DMF (6 mL) and to the stirred solution K2CO3 (13.8 mg, 1 mmol) and 2-bromoacetamide (138 mg, 1 mmol) were added. The mixture was stirred at room temperature overnight. The suspension was concentrated in vacuo, and the residue was partitioned between water (20 mL) and CH2Cl2 (10 mL). The aqueous phase was separated and extracted with CH2Cl2 (20 mL×2). The combined organic phases were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 80/20), to give 79 as a white solid (226 mg, 90%). 1H NMR (CDCl3, 300 MHz) δ7.88 (br s, 1H), 7.27-7.18 (m, 2H), 6.76 (d, J=8.7 Hz, 1H), 5.54 (br s, 1H), 4.78( br s, 1H), 4.47 (s, 1H), 4.36 (d, J=6.3 Hz), 1.43 (s, 9H). MS (m/e) (API-ES) 337.0 (MNa)+. m.p 142-143° C.

Workup

  1. additionwere added
  2. concentrationThe suspension was concentrated in vacuo
  3. customthe residue was partitioned between water (20 mL) and CH2Cl2 (10 mL)
  4. customThe aqueous phase was separated
  5. extractionextracted with CH2Cl2 (20 mL×2)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate 80/20)

Sources & evidence

ORD record
ord-e441d0329c4449f8b66c95c270da2db3
Source dataset
uspto-grants-2010_11
Patent number
US07825126B2

Reaction notes

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