Sodium Hydroxide → HCID 68486860, compound

HRID 1259451Notes

Reaction equation

[OH:1][CH2:2][C@H:3]1[CH2:8][O:7][C:6]2[CH:9]=[CH:10][C:11]([N+:17]([O-])=O)=[C:12]([CH2:13][C:14](O)=[O:15])[C:5]=2[O:4]1.[OH-].[Na+].[H][H]>[Pd]>[OH2:1].[OH:1][CH2:2][C@@H:3]1[O:4][C:5]2=[C:12]3[C:11](=[CH:10][CH:9]=[C:6]2[O:7][CH2:8]1)[NH:17][C:14](=[O:15])[CH2:13]3

Participants

Conditions

Temperature: 65 °C

Procedure

A Parr hydrogenation shake flask is charged with [(3S)-3-(hydroxymethyl)-6-nitro-2,3-dihydro-1,4-benzodioxin-5-yl]acetic acid (20.00 g, 74.2 mmol), NaOH (0.33 N, 300 mL, 99 mmol) and palladium (10% on carbon, 1.6 g). The vessel is pressurized to 50 psi with hydrogen and shaken for 3 h, at which point the pressure is released and the mixture is filtered through celite. The solution is acidified with concentrated. HCl (20 mL) and heated to 65° C. for 7 h. The heating is discontinued, and the suspension is stirred overnight. The precipitate is collected by vacuum filtration, and the filter cake is washed with water (50 mL) and dried under suction to give the title compound (13.81 g, 84%) as a tan powder. LCMS (Standard Method): 1.81 min, 222 (M+H)+. 1NMR (300 MHz, DMSO-d6) δ 10.17 (br s, 1H), 6.66 (d, J=8.2 Hz, 1H), 6.27 (d, J=8.2, 1H), 5.03 (br s, 1H), 4.25-4.13 (m, 2H), 3.98-3.91 (m, 1H), 3.65-3.57 (m, 2H), 3.31 (br s, 4H).

Workup

filtrationthe mixture is filtered through celite
concentrationwith concentrated
stirringthe suspension is stirred overnight
filtrationThe precipitate is collected by vacuum filtration
washthe filter cake is washed with water (50 mL)
customdried under suction

Sources & evidence

ORD record: ord-f613db2341a445239a1c0dd70fac8ea3
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08466296B2

Reaction notes

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