Lithium Hydroxide → 2-(4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoylamino)-2-methyl-propionic acid

HRID 736522Notes

Reaction equation

C[O:2][C:3](=[O:37])[C:4]([NH:7][C:8](=[O:36])[C:9]1[CH:14]=[CH:13][C:12]([C:15]([CH2:33][CH3:34])([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]([CH2:30][CH3:31])([OH:29])[CH2:27][CH3:28])=[C:20]([CH3:32])[CH:19]=2)[CH2:16][CH3:17])=[CH:11][C:10]=1[CH3:35])([CH3:6])[CH3:5].[OH-].[Li+]>>[CH2:16]([C:15]([C:12]1[CH:13]=[CH:14][C:9]([C:8]([NH:7][C:4]([CH3:5])([CH3:6])[C:3]([OH:37])=[O:2])=[O:36])=[C:10]([CH3:35])[CH:11]=1)([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[C:25][C:26]([CH2:27][CH3:28])([OH:29])[CH2:30][CH3:31])=[C:20]([CH3:32])[CH:19]=1)[CH2:33][CH3:34])[CH3:17]

Participants

Reactant 2

HCID 3939Lithium Hydroxide

HCID 578493282-(4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoylamino)-2-methyl-propionic acid methyl ester

Product 1

HCID 112140352-(4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoylamino)-2-methyl-propionic acidYield 99.5%

Procedure

2-(4-{1-Ethyl-1-[4-(3-ethyl-3-hydroxy-pent-1-ynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoylamino)-2-methyl-propionic acid methyl ester (3.97 mg, 0.785 mmol) and lithium hydroxide (56 mg, 2.36 mmol) are reacted and purified analogous to Example 1I to give the title compound (384 mg, 99%).

Workup

custompurified analogous to Example 1I

Sources & evidence

ORD record: ord-a08ca645fd1049dba6f52249778fe640
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595345B2

Reaction notes

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