Hydrochloric Acid → HCID 14478553, compound

HRID 1199243Notes

Reaction equation

[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C@:20]([O:24][C:25]([C:27]1[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:26])([C:22]#[CH:23])[CH3:21])(=[O:3])[CH3:2].C[C@@H](C1C=CC=CC=1)N.Cl>C(Cl)Cl.CCOCC>[C:1]([O:4][C:5]1[C:10]([CH3:11])=[C:9]([CH3:12])[C:8]([O:13][C:14](=[O:16])[CH3:15])=[C:7]([CH3:17])[C:6]=1[CH2:18][CH2:19][C@:20]([O:24][C:25]([C:27]1[C:28]([C:33]([OH:35])=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:26])([C:22]#[CH:23])[CH3:21])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of (S)-1,2-benzenedicarboxylic acid[3-[2,5-bis (acetyloxy)-3,4,6-trimethylphenyl]-1-ethynyl-1-methylpropyl] ester-(S)-α-methyl benzenemethanamine (1:1) (salt) (110 g, 0.17 mol), 400 mL of 1.0N HCl, and 40 mL of CH2Cl2 -ether (1:9) was stirred vigorously for 1.0 h at 25° C. It was then extracted with ether (2×200 mL). The ether extracts were combined, washed with 1.0N HCl (200 mL), water (200 mL), and dried over anhydrous MgSO4. Evaporation of ether in vacuo gave a solid which was further dried at 25° C./0.5 mm for 16 h to afford 80.59 of (S)-1,2-benzenedicarboxylic acid [3-[2,5-bis(acetyloxy)-3,4,6-trimethylphenyl]-1-ethynyl-1-methylpropyl]ester as a white foam: [α]D25 +15.95° (c 0.96, ethanol).

Workup

extractionIt was then extracted with ether (2×200 mL)
washwashed with 1.0N HCl (200 mL), water (200 mL)
dry with materialdried over anhydrous MgSO4
customEvaporation of ether in vacuo
customgave a solid which
customwas further dried at 25° C./0.5 mm for 16 h

Sources & evidence

ORD record: ord-75ec02a760274d8cae482ea58ccc2ad4
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04898962

Reaction notes

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