Acetic Acid → HCID 117720336, compound

HRID 1854579Notes

Reaction equation

[Si]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][C:22]([OH:25])([CH3:24])[CH3:23])[C@H:12]([CH3:26])[N:11]1[C:27](=[O:38])[CH2:28][C:29]1[C:34]([O:35][CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[Cl:37])(C(C)(C)C)(C)C.C(O)(=O)C.O>C1COCC1>[Cl:37][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]([O:35][CH3:36])[C:29]=1[CH2:28][C:27]([N:11]1[C@@H:10]([CH2:9][OH:8])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH2:20][CH2:21][C:22]([OH:25])([CH3:23])[CH3:24])[C@@H:12]1[CH3:26])=[O:38]

Participants

Conditions

Temperature: 50 °C

Procedure

Dissolve 1-[(1S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(3-hydroxy-3-methyl-butyl)-1-methyl-3,4-dihydro-1H-isoquinolin-2-yl]-2-(2-chloro-6-methoxy-phenyl)ethanone (0.58 g, 1.04 mmol) in THF (5.3 mL). Add acetic acid (16 mL, 279 mmol) and water (5.3 mL). Stir at 50° C. for 1.5 hours. Concentrate under reduced pressure. Dissolve the residue in ethyl acetate and wash with saturated sodium bicarbonate solution, water, and brine. Dry over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography, eluting with acetone: hexanes (gradient, 0-30%) to give the title compound as a white foam (0.34 g, 0.76 mmol). MS (m/z): 446.0 (M+1).

Workup

concentrationConcentrate under reduced pressure
dissolutionDissolve the residue in ethyl acetate
washwash with saturated sodium bicarbonate solution, water, and brine
dry with materialDry over sodium sulfate
filtrationfilter
concentrationconcentrate under reduced pressure
customPurify the residue by silica gel chromatography
washeluting with acetone

Sources & evidence

ORD record: ord-73972013b1ee400d823fb98c5911a509
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962654B2

Reaction notes

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