Lithium hydroxide, monohydrate → HCID 16040643, compound

HRID 733602Notes

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:43]=[CH:42][C:16]([CH2:17][N:18]([C:33](=[O:41])[CH2:34][CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:19]3[C:28]4[CH:27]=[C:26]([C:29]([O:31]C)=[O:30])[CH:25]=[CH:24][C:23]=4[CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].O[Li].O>>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:43]=[CH:42][C:16]([CH2:17][N:18]([C:33](=[O:41])[CH2:34][CH2:35][CH:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[CH:19]3[C:28]4[CH:27]=[C:26]([C:29]([OH:31])=[O:30])[CH:25]=[CH:24][C:23]=4[CH2:22][CH2:21][CH2:20]3)=[CH:15][CH:14]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 168937Lithium hydroxide, monohydrate

HCID 57841395HCID 57841395, compound

Product 1

HCID 16040643HCID 16040643, compound

Procedure

The titled compound was prepared following the procedure F using methyl 8-[{4-[(4-butylphenyl)ethynyl]benzyl}(3-cyclopentylpropanoyl)amino]-5,6,7,8-tetrahydro-2-naphthalenecarboxylate and LiOH.H2O, as a white solid (94%). 1H NMR (MeOD, 300 MHz) δ 7.80 (m, 1H), 7.71 (d, J=5.5 Hz. 1H), 7.47 (d, J=7.5 Hz, 1H), 7.38 (m, 3H), 7.18 (m, 5H), 5.94 (m, 0.5H), 5.30 (m, 0.5H), 4.80 (m, 1H), 4.63 (d, J=18.3 Hz, 0.5H), 4.21 (d, J=18.3 Hz, 0.5H), 2.81 (m, 2H), 2.62 (m, 2H), 2.45 (m, 1H), 2.27 (m, 1H), 2.10-1.06 (m, 19H), 0.93 (t, J=7.2 Hz, 3H). M− (ESI): 560.3; M+ (ESI): 562.2. HPLC, Rt: 5.97 min (Purity: 99.2%).

Sources & evidence

ORD record: ord-9493ffbbe5a145efb97e7ede89f3c16c
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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