Potassium Carbonate → (4-Oxazol-5-yl-naphthalen-1-yl)-carbamic acid tert-butyl ester

HRID 1441840Notes

Reaction equation

HRID 1441840 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]#N)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C([O:25][C:26](=O)[NH:27][C:28]1C2C(=CC=CC=2)C(C=O)=CC=1)(C)(C)C.C1(C)C(S([N+]#[C-])(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([C:18]2[O:25][CH:26]=[N:27][CH:28]=2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 21875242Toluene-sulfonylisocyanideHCID 58745930(4-Cyano-naphthalen-1-yl)-carbamic acid tert-butyl ester2×HCID 58745967tert-Butyl 4-formylnaphthalen-1-ylcarbamate

Product 1

HCID 58745848(4-Oxazol-5-yl-naphthalen-1-yl)-carbamic acid tert-butyl esterYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above mixture of compounds 503A & 503B (3.37 g, 10.0 mmol; corrected for presence of compound 503A), toluene-sulfonylisocyanide (2.15 g, 11.0 mmol) and potassium carbonate (1.66 g, 12.0 mmol) in 50 mL of methanol was refluxed for 4 h. The reaction mixture was partitioned between water (200 mL) and chloroform (200 mL). After extracting the aqueous layer with chloroform (100 mL), the combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel eluting with a gradient of 10-40% ethyl acetate in hexane to give 1.35 g (44%) of compound 503C as a white solid. 1HNMR (400 MHz, DMSO-d6): δ 9.45 (s, 1H), 8.57 (s, 1H), 8.20 (m, 2H), 7.76 (m, 2H), 7.64 (s, 1H), 7.62 (m, 2H), 1.51 (s, 9H).

Workup

  1. temperaturewas refluxed for 4 h
  2. customThe reaction mixture was partitioned between water (200 mL) and chloroform (200 mL)
  3. extractionAfter extracting the aqueous layer with chloroform (100 mL)
  4. dry with materialthe combined organic layers were dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by flash chromatography on silica gel eluting with a gradient of 10-40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-23817901c61c42f2a446cf2b028513fc
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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