tert-Butanol → HCID 67252110, compound

HRID 1798234Notes

Reaction equation

HRID 1798234 reaction equation
C([O:3][C:4]([CH2:6][CH:7]1[O:11][B:10]([OH:12])[C:9]2[CH:13]=[C:14]([O:18][C:19]3[N:20]=[CH:21][C:22](C(O)=O)=[N:23][CH:24]=3)[CH:15]=[C:16]([CH3:17])[C:8]1=2)=[O:5])C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:35])C=CC=CC=1.C([N:47]([CH2:50]C)CC)C.[CH3:52][C:53]([OH:56])([CH3:55])[CH3:54]>>[C:53]([O:56][C:50]([NH:47][C:22]1[N:23]=[CH:24][C:19]([O:18][C:14]2[CH:15]=[C:16]([CH3:17])[C:8]3[CH:7]([CH2:6][C:4]([OH:3])=[O:5])[O:11][B:10]([OH:12])[C:9]=3[CH:13]=2)=[N:20][CH:21]=1)=[O:35])([CH3:55])([CH3:54])[CH3:52]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 67252166HCID 67252166, compound

Product 1

HCID 67252110HCID 67252110, compoundYield 27%

Conditions

Temperature
95 °C

Procedure

To a solution of 5-(3-ethoxycarbonylmethyl-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yloxy)-pyrazine-2-carboxylic acid (500 mg, 1.34 mmol) in tBuOH (10 mL) was added diphenylphosphoryl azide (0.35 mL, 1.61 mmol) and triethylamine (0.41 mL, 2.95 mmol). The reaction mixture was heated to 95° C. for 2 h. The solvent was removed under vacuum and the residue was extracted with ethyl acetate, washed with water and brine. The organic portion was dried by Na2SO4 and concentrated. The residue was purified by column chromatography (silica, DCM/MeOH=20:1) affording the title compound (155 mg, 27%) as a white solid. 1H NMR (CDCl3) δ 8.79 (s, 1H), 8.02 (s, 1H), 7.20 (d, 1H), 7.03 (d, 1H), 5.63 (dd, 1H), 4.19 (q, 2H), 3.08 (dd, 1H), 2.42 (m, 1H), 2.38 (s, 3H), 1.57 (s, 9H), 1.26 (t, 3H).

Workup

  1. customThe solvent was removed under vacuum
  2. extractionthe residue was extracted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic portion was dried by Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (silica, DCM/MeOH=20:1)

Sources & evidence

ORD record
ord-42537c073ba74b2eafccde38a314ad4f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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