Hydrochloric Acid → HCID 57971644, compound

HRID 2360665Notes

Reaction equation

C1([O:6][C:7](=[O:47])[C@@H:8]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([CH2:24][NH:25][CH2:26][C:27]3[CH:28]=[CH:29][C:30]4[CH:34]=[C:33]([C:35](=[O:45])[NH:36][O:37][CH:38]([O:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH3:39])[S:32][C:31]=4[CH:46]=3)=[CH:20][CH:19]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)CCCC1.[Li+].[OH-].Cl>C1COCC1.O>[CH2:41]([O:40][CH:38]([O:37][NH:36][C:35]([C:33]1[S:32][C:31]2[CH:46]=[C:27]([CH2:26][NH:25][CH2:24][C:21]3[CH:20]=[CH:19][C:18]([CH2:17][NH:16][C@@H:8]([CH2:9][C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=4)[C:7]([OH:47])=[O:6])=[CH:23][CH:22]=3)[CH:28]=[CH:29][C:30]=2[CH:34]=1)=[O:45])[CH3:39])[CH:42]([CH3:44])[CH3:43]

Participants

Conditions

Temperature: 50 °C

Procedure

(S)-2-[4-({[2-(1-Isobutoxy-ethoxycarbamoyl)-benzo[b]thiophen-6-ylmethyl]-amino}-methyl)-benzylamino]-3-phenyl-propionic acid cyclopentyl ester (40 mg, 0.06 mmol) was dissolved in THF (2 mL) and water (2 mL). LiOH (8 mg, 0.30 mmol) was added and the reaction mixture heated to 50° C. for 36 h. THF was removed by evaporation and the residue partitioned between water (10 mL) and EtOAc (10 mL). The aqueous layer was isolated and the pH adjusted to 3 by addition of 1M HCl. This was extracted with EtOAc (3×20 mL), the organic layers combined and evaporated to dryness.

Workup

customTHF was removed by evaporation
customthe residue partitioned between water (10 mL) and EtOAc (10 mL)
customThe aqueous layer was isolated
extractionThis was extracted with EtOAc (3×20 mL)
customevaporated to dryness

Sources & evidence

ORD record: ord-332ac98adc8c487493d2ea08b79fecbe
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686032B2

Reaction notes

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