Methanol → BI-135585

HRID 1406611Notes

Reaction equation

[OH-:1].[K+].[CH3:3][OH:4].O[C@:6]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([CH2:35][C:36](O)([CH3:38])[CH3:37])[CH2:7][CH2:8][N:9]([C@H:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][N:30]([CH3:33])[C:29](=[O:34])[CH:28]=2)=[CH:23][CH:22]=1)[CH3:20])C(=O)OC1C=CC=CC=1.[OH2:46]>CN1CCCC1=O>[OH:1][C:36]([CH3:38])([CH3:37])[CH2:35][C@@:6]1([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[O:4][C:3](=[O:46])[N:9]([C@H:19]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][N:30]([CH3:33])[C:29](=[O:34])[CH:28]=3)=[CH:23][CH:22]=2)[CH3:20])[CH2:8][CH2:7]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 25% KOH in MeOH (1.21 g, 5.41 mmol) is added to a solution of 14 (1.00 g, 1.80 mmol) in 1-methylpyrrolidin-2-one (NMP, 4 mL). The resultant mixture is stirred at about 25° C. for 15 h, treated with water (15 mL), and stirred at 25° C. for 0.5 h. The resultant solids are collected via filtration, rinsed with MeOH/water (⅓, 20 mL), and dried to provide 13 as white solid. Yield: 0.68 g, 81.4%. Purity: 99.6 area % at 220 nm. 1H NMR (DMSO-d6, 500 MHz): δ 7.74 (d, J=7.1 Hz, 1H), 7.43 (d, J=7.7 Hz, 2H), 7.34 (m, 5H), 6.95 (d, J=7.7 Hz, 2H), 6.56 (s, 1H), 6.47 (d, J=6.0 Hz, 1H), 5.43 (m, 1H), 4.26 (s, 1H), 3.43 (s, 3H, 3.33 (s, 2H), 3.02 (m, 1H), 2.43 (m, 1H), 2.14 (m, 1H), 2.02 (s, 2H), 1.46 (d, J=6.8 Hz, 3H), 1.18 (s, 3H), 0.87 (s, 3H); 13C NMR (DMSO-d6, 400 MHz): δ 161.93, 152.44, 150.05, 143.37, 141.24, 139.85, 135.32, 128.33, 127.22, 127.10, 126.26, 124.90, 114.68, 103.70, 83.04, 69.30, 54.01, 52.62, 36.35, 36.22, 31.51, 30.81, 29.91, 15.46.

Workup

filtrationThe resultant solids are collected via filtration
washrinsed with MeOH/water (⅓, 20 mL)
customdried

Sources & evidence

ORD record: ord-f80717727fa84835a97691421060401a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916701B2

Reaction notes

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