Hydrochloric Acid → HCID 67105892, compound

HRID 885273Notes

Reaction equation

HRID 885273 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[NH:10][C@H:11]([C:13](=[O:18])N(OC)C)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1.C([Mg]Cl)(C)C.Cl>C1COCC1>[CH2:1]([O:8][C:9](=[O:19])[NH:10][C@@H:11]([CH3:12])[C:13]([C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1)=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7806p-BromochlorobenzeneHCID 10515879(S)-Benzyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamateHCID 178418918HCID 178418918, compound

Product 1

HCID 67105892HCID 67105892, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

[(S)-1-(Methoxy-methyl-carbamoyl)-ethyl]-carbamic acid benzyl ester (1 g, 3.8 mmol) and 4-bromochlorobenzene (0.9 g, 4.7 mmol) were dissolved in THF (10 mL). The solution was degassed with N2 for 5 minutes, and then cooled to 0° C. Isopropylmagnesium chloride (2M in THF; 4.7 mL, 9.4 mmol) was added slowly, and the reaction was stirred at room temperature for 2 hours. Once no starting material was seen by analytical tlc, the mixture was cooled to 0° C. 1N Aqueous HCl was added, and the organic layer was separated and washed with brine. After concentrating, the crude material was purified by silica gel chromatography to give the desired product as a colorless oil (1 g).

Workup

  1. customThe solution was degassed with N2 for 5 minutes
  2. temperaturethe mixture was cooled to 0° C
  3. customthe organic layer was separated
  4. washwashed with brine
  5. concentrationAfter concentrating
  6. customthe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0630984f4e624bf492e422f770b1559e
Source dataset
uspto-grants-2012_08
Patent number
US08242145B2

Reaction notes

Loading…