Potassium Carbonate → HCID 118114363, compound

HRID 2284858Notes

Reaction equation

HRID 2284858 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:30][C:31]1[O:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=1>CN(C=O)C>[C:18]([O:17][C:16]([NH:15][C@@H:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][CH2:30][C:31]1[O:32][CH:33]=[C:34]([C:36]([O:38][CH3:39])=[O:37])[N:35]=1)=[O:22])([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2763199Methyl 2-(chloromethyl)oxazole-4-carboxylateHCID 90209372(S)-tert-butyl((3-hydroxyphenyl)(phenyl)methyl)carbamate

Product 1

HCID 118114363HCID 118114363, compoundYield 113.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of (S)-tert-butyl ((3-hydroxyphenyl)(phenyl)methyl)-carbamate (I8, 1 g, 3.34 mmol) in DMF (9.4 mL) at 0° C. under nitrogen was added K2CO3 (0.693 g, 5.01 mmol) followed by methyl 2-(chloromethyl)oxazole-4-carboxylate (0.586 g, 3.34 mmol). After 10 minutes at 0° C., the reaction was allowed to warm to room temperature and the stirring was maintained for 21 h. The reaction mixture was then partitioned between water (10 mL) and ethyl acetate (10 mL). The aqueous phase was extracted with ethyl acetate (2×20 mL) and the combined organic phases were dried over MgSO4, filtered then concentrated in vacuo to give the title compound (1.66 g) as an off-white solid. The residue was taken on to the next step without further purification. LCMS (Method 1): [MH+]=439 at 4.22 min.

Workup

  1. temperaturethe stirring was maintained for 21 h
  2. customThe reaction mixture was then partitioned between water (10 mL) and ethyl acetate (10 mL)
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×20 mL)
  4. dry with materialthe combined organic phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-ad36bd5f272d436da28eb356cf5e9cb9
Source dataset
uspto-grants-2015_09
Patent number
US09145409B2

Reaction notes

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