Methanol → [4-(2-Cyclopropyl-4,4-dimethyl 1,2,3,4-tetrahydro-isoquinoline-6-yl-ethynyl)-2-fluoro-phenyl]-acetic Acid

HRID 51650Notes

Reaction equation

HRID 51650 reaction equation
C([O:3][C:4](=[O:30])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[CH2:20][N:19]([CH:24]2[CH2:26][CH2:25]2)[CH2:18][C:17]3([CH3:28])[CH3:27])=[CH:8][C:7]=1[F:29])C.CO.O1CCCC1.O.[OH-].[Li+]>O>[CH:24]1([N:19]2[CH2:18][C:17]([CH3:28])([CH3:27])[C:16]3[C:21](=[CH:22][CH:23]=[C:14]([C:13]#[C:12][C:9]4[CH:10]=[CH:11][C:6]([CH2:5][C:4]([OH:30])=[O:3])=[C:7]([F:29])[CH:8]=4)[CH:15]=3)[CH2:20]2)[CH2:26][CH2:25]1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 69548286[4-(2-Cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ylethynyl)-2-fluoro-phenyl]-acetic acid ethyl ester2×

Product 1

HCID 10134200[4-(2-Cyclopropyl-4,4-dimethyl 1,2,3,4-tetrahydro-isoquinoline-6-yl-ethynyl)-2-fluoro-phenyl]-acetic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Following general procedure J and using [4-(2-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinolin-6-ylethynyl)-2-fluoro-phenyl]-acetic acid ethyl ester (Compound 21, 0.055 g, 0.135 mmol), methanol (2 mL), tetrahydrofuran (4 mL), water (1 mL) and lithium hydroxide monohydrate (0.117 g, 2.97 mmol) the title compound was obtained as a pale yellow solid foam (0.040 g, 78%).

Sources & evidence

ORD record
ord-10a69cc50ec44009a789976b23fb21ae
Source dataset
uspto-grants-2004_03
Patent number
US06713647B2

Reaction notes

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