(5S)-6-tert-Butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[2-(4-hydroxyphenyl)ethyl]-6-oxohexanoic acid → Di-tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-5-[2-(4-hydroxyphenyl)ethyl]hexanedioate

HRID 591314Notes

Reaction equation

[C:1]([O:5][C:6](=[O:38])[C@@H:7]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:8][CH2:9][C:10]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)C(O)=O)([CH3:4])([CH3:3])[CH3:2]>O1CCOCC1>[C:34]([O:33][C:31]([NH:30][C@@H:7]([CH2:8][CH2:9][CH:10]([CH2:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:38])=[O:32])([CH3:35])([CH3:36])[CH3:37]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 370 mg (5S)-6-tert-butoxy-2-(tert-butoxycarbonyl)-5-[(tert-butoxycarbonyl)amino]-2-[2-(4-hydroxyphenyl)ethyl]-6-oxohexanoic acid (0.69 mmol) in 1,4-dioxane (30 mL) was added 210 mg of 4-N,N-dimethylaminopyridine (1.72 mmol) and the mixture was stirred overnight at 100° C. (bath temperature), followed by refluxing for another 18 h. After cooling to room temperature, the mixture was concentrated in vacuo. The residue was purified by preparative HPLC (Method A) to give 169 mg (50% yield) of the target compound. In addition, 38 mg of unreacted starting material were recovered.

Workup

temperatureby refluxing for another 18 h
temperatureAfter cooling to room temperature
concentrationthe mixture was concentrated in vacuo
customThe residue was purified by preparative HPLC (Method A)

Sources & evidence

ORD record: ord-cb14b7cc7562478da0b859253ca1066a
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238631B2

Reaction notes

Loading…