Potassium Carbonate → HCID 91615104, compound

HRID 1669506Notes

Reaction equation

HRID 1669506 reaction equation
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:11]([O:13][CH3:14])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.F[C:23]1[CH:36]=[CH:35][C:26]([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:28])=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:18]([O:17][C:15]([NH:1][C@@H:2]([CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][C:32]2[CH:33]=[CH:34][C:29]([C:27](=[O:28])[C:26]3[CH:35]=[CH:36][CH:23]=[CH:24][CH:25]=3)=[CH:30][CH:31]=2)=[CH:8][CH:9]=1)[C:11]([O:13][CH3:14])=[O:12])=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 676634-FluorobenzophenoneHCID 7019130Boc-Tyr-OMe

Product 1

HCID 91615104HCID 91615104, compoundYield 102.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of Boc-Tyr-OMe (0.80 g, 2.7 mmol), 4-fluorobenzophenone (0.80 g, 4.0 mmol) and potassium carbonate (1.11 g, 8.0 mmol) in DMF (30 mL) was heated to 100° C. After 42 h, the reaction mixture was allowed to cool to rt. DMF was removed in vacuo and the remaining material was partitioned between EtOAc (50 mL) and water (50 mL). This gave an emulsion that was allowed to sit overnight. The following day the layers had mostly separated and so the organic layer was concentrated in vacuo to give 1.32 g of material. This material was purified by chromatography (4:1 hexane/ethyl acetate) to give 0.69 g of product. 1H NMR (400 MHz, CDCl3) δ 1.43 (s, 9H), 2.98-3.19 (m, 2H), 3.74 (s, 3H), 4.60 (q, J=6.8 Hz, 1H), 5.03 (br d, J=7.6 Hz, 1H), 6.98-7.05 (m, 4H), 7.14-7.19 (m, 2H), 7.45-7.51 (m, 2H), 7.55-7.61 (m, 1H), 7.75-7.84 (m, 4H).

Workup

  1. temperatureto cool to rt
  2. customDMF was removed in vacuo
  3. customthe remaining material was partitioned between EtOAc (50 mL) and water (50 mL)
  4. customThis gave an emulsion that
  5. waitto sit overnight
  6. customThe following day the layers had mostly separated and so the organic layer
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-80da8ba6cfd5498b92d2120dbd1b6de3
Source dataset
uspto-grants-2011_08
Patent number
US07989480B2

Reaction notes

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