Acetic Acid → HCID 67300348, compound

HRID 1015523Notes

Reaction equation

[OH-].[Na+].BrBr.Br[O-].[C:7]([C:10]12[CH2:17][CH:16]3[CH2:18][C:12]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH2:13][CH:14]1[CH2:15]3)[CH2:11]2)(=[O:9])C.C(O)(=[O:29])C>O1CCOCC1.O>[C:22]([O:21][C:20]([NH:19][C:12]12[CH2:18][CH:16]3[CH2:15][CH:14]([CH2:13]1)[C:10]([C:7]([OH:9])=[O:29])([CH2:17]3)[CH2:11]2)=[O:26])([CH3:23])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of NaOH (1.32 g, 33.0 mmol), H2O (8.8 mL), and 1,4 dioxane (2 mL) at ice bath temperature was added Br2 (0.6 mL, 12.3 mmol) and stirred for 5 minutes. The resulting hypobromite solution was added dropwise to a stirred solution of the compound obtained in step II (0.6 g, 2.2 mmol) in 1,4-dioxane (2.4 mL) at around 10° C. The reaction mixture was gradually warmed to r.t, stirred for 1 h, then cooled to 0° C. and quenched by adding acetic acid (2 mL, 36.3 mmol). The mixture was diluted with water and extracted in EtOAc. The combined organic layer was washed with brine, dried over Na2SO4 and the solvent was removed under reduced pressure to obtain 1-[(tert-butoxycarbonyl)amino]tricyclo[3.3.1.03,7]nonane-3-carboxylic acid (0.54 g) as a viscous liquid in 87% yield. m/z (M−1) 280; 1H NMR (CDCl3) 300 MHz δ 4.75 (s (br), 1H), 2.78-2.60 (m, 1H), 2.47-2.40 (m, 1H), 2.33-2.22 (m, 1H), 2.18-1.72 (m, 8H), 1.62-1.53 (m, 1H), 1.43 (s, 9H).

Workup

temperatureThe reaction mixture was gradually warmed
stirringstirred for 1 h
customquenched
extractionextracted in EtOAc
washThe combined organic layer was washed with brine
dry with materialdried over Na2SO4
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-f4581a27c8f74377b6037a7678f8fbcd
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07985759B2

Reaction notes

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