Sodium Hydroxide → HCID 67365596, compound

HRID 217939Notes

Reaction equation

[OH-].[Na+].C[O:4][C:5](=[O:24])[C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[CH:8][CH:7]=1>C1COCC1>[C:20]([O:19][C:17]([NH:16][CH2:15][CH2:14][CH2:13][CH2:12][C:9]1[CH:8]=[CH:7][C:6]([C:5]([OH:24])=[O:4])=[CH:11][CH:10]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

An aqueous (10 mL) solution of sodium hydroxide (0.53 g, 13.18 mmol) was added into the solution of 25 (1.35 g, 4.39 mmol) in THF (60 mL) and the resulting solution was stirred at room temperature for 48 h and at 60° C. for 14 h. Then the solvent was removed under reduced pressure. Water (20 mL) was added and pH was adjusted to 7 with HCl. The white solid precipitate was filtered off, washed with water and dried under vacuum. 1.22 g (95%) of white solid 26 was obtained. 1H NMR (300 MHz, DMSO-d6) δ 1.39 (br s, 11H), 1.52 (m, 2H), 1.64 (m, 2H), 2.92 (m, 2H), 6.84 (m, 1H), 7.28 (d, 2H), 7.85 (d, 2H).

Workup

customThen the solvent was removed under reduced pressure
additionWater (20 mL) was added
filtrationThe white solid precipitate was filtered off
washwashed with water
customdried under vacuum

Sources & evidence

ORD record: ord-1d7c69cf13824d6a8528ad6eb1834502
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198286B2

Reaction notes

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