tert-Butanol → Ethyl 6-[(tert-butoxycarbonyl)amino]pyridine-2-carboxylate

HRID 2060089Notes

Reaction equation

[CH3:1][CH2:2][O:3][C:4]([C:6]1[N:11]=[C:10](C(O)=O)[CH:9]=[CH:8][CH:7]=1)=[O:5].C([N:18]([CH2:22]C)C(C)C)(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])=CC=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>C1(C)C=CC=CC=1>[CH2:2]([O:3][C:4]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:18][C:22]([O:45][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:31])[N:11]=1)=[O:5])[CH3:1]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2,6-pyridinedicarboxylate monoethyl ester 1 (1.25 g, 6.40 mmol, 1.00 equiv) and N,N-diisopropylethylamine (2.2 mL, 12.8 mmol, 2.00 equiv) in toluene (38 mL) and tert-butanol (3.8 mL) was added DPPA (1.9 mL, 8.8 mmol, 1.4 equiv). The resulting solution was heated at 100° C. for 5 hr, cooled and partitioned between ethyl acetate and water, washed with brine and dried (sodium sulfate). Purification by chromatography (15% ethyl acetate in hexanes) afforded 6-tert-butoxycarbonylamino-pyridine-2-carboxylic acid ethyl ester (0.88 g, 51%) as a yellow semisolid 348. LCMS: (MH)+=267.1 (rt=1.95 min).

Workup

temperaturecooled
custompartitioned between ethyl acetate and water
washwashed with brine
dry with materialdried (sodium sulfate)
customPurification by chromatography (15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-cc94008a9bb0433aa3a4888c235949be
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278337B2

Reaction notes

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