Hydrochloric Acid → HCID 67087079, compound

HRID 390406Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8](C(OC(C)(C)C)=O)[CH2:7]2)[CH2:3][CH2:2]1.[F:22][C:23]1[CH:28]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=2)[CH:26]=[CH:25][C:24]=1[CH2:38][CH2:39][C:40]([OH:42])=[O:41].[ClH:43].[CH3:44]O>>[ClH:43].[F:22][C:23]1[CH:28]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([CH2:37][N:1]3[CH2:2][CH2:3][C:4]4([C:14]5[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=5)[NH:8][CH2:7]4)[CH2:5][CH2:6]3)=[CH:33][CH:32]=2)[CH:26]=[CH:25][C:24]=1[CH2:38][CH2:39][C:40]([O:42][CH3:44])=[O:41]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 887Methanol2×

HCID 67087265HCID 67087265, compound

Product 1

HCID 67087079HCID 67087079, compoundYield 64%

Procedure

To a solution of tert-butyl spiro[indole-3,4′-piperidine]-1(2H)-carboxylate-3-{2-fluoro-4-[(4-methylbenzyl)oxy]phenyl}propanoic acid (0.12 g, 0.208 mmol) in methanol (5 mL), is added HCl in methanol (4 M, 5 mL) at 0° C. The reaction mixture is allowed to warm to room temperature and stirred for 1 hour. The reaction mixture is evaporated to dryness to give the title compound as a pale yellow solid (0.07 g, 64%). ESI/MS m/z 489.6 (M+H)+.

Workup

customThe reaction mixture is evaporated to dryness

Sources & evidence

ORD record: ord-531233acbeb9475582a3b0722350df5e
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383642B2

Reaction notes

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