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

HRID 841336Notes

Reaction equation

HRID 841336 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-5dc0ca27718d472d8ae727f841f45fc7
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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