Hydrochloric Acid → HCID 58505559, compound

HRID 1917609Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:20]=[CH:19][C:18]2[N:14]([C:15]([C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])=[C:16]([CH2:30][C:31]([CH3:38])([CH3:37])[C:32]([O:34]CC)=[O:33])[C:17]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[O:22])[CH:13]=1.[OH-].[Na+].Cl>C1COCC1.CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[CH:20]=[CH:19][C:18]2[N:14]([C:15]([C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])=[C:16]([CH2:30][C:31]([CH3:38])([CH3:37])[C:32]([OH:34])=[O:33])[C:17]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[O:22])[CH:13]=1

Participants

Conditions

Temperature: 23 °C

Procedure

A solution of ethyl 3-[6-(1,3-benzothiazol-2-ylmethoxy)-1-[(4-chlorophenyl)carbonyl]-3-(2,2-dimethylpropanoyl)indolizin-2-yl]-2,2-dimethylpropanoate (74 mg, 0.12 mmol) in THF (0.5 mL), MeOH (1.0 mL), and 6M aqueous NaOH (1.0 mL) is heated at 70° C. for 1 h then cooled to 23° C. and acidified to pH=1 with concentrated aqueous HCl. The mixture is partitioned between CH2Cl2 and brine and organics are collected, dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, CH2Cl2 to 10% MeOH in CH2Cl2) gives the title compound (59 mg, 83%).

Workup

customThe mixture is partitioned between CH2Cl2 and brine
customorganics are collected
dry with materialdried with MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the crude by flash chromatography (SiO2, CH2Cl2 to 10% MeOH in CH2Cl2)

Sources & evidence

ORD record: ord-aa5f1dfdcf964612a7ce4d8200db90a5
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618300B2

Reaction notes

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