Hydrochloric Acid → HCID 57907509, compound

HRID 403432Notes

Reaction equation

C([O:3][C:4](=[O:23])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH:7]=1)C.C(O)C.[Li+].[OH-].Cl>C1COCC1.O>[CH2:16]([O:15][C:13]([NH:12][C:8]1[CH:7]=[C:6]([CH2:5][C:4]([OH:23])=[O:3])[CH:11]=[CH:10][CH:9]=1)=[O:14])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 44.0 g (140 mmol) of ethyl(3-{[(benzyloxy)carbonyl]amino}phenyl)acetate) (from Step A) in THF, ethanol, and water (1:1:1, 1500 mL) was added solid LiOH (16.8 g, 700 mmol) and the resulting solution heated to 60° C. via oil bath for 3 h. The mixture was cooled to room temperature overnight and then 40 mL of concentrate HCl was slowly added, keeping the temperature below 25° C., until the solution was about pH of 2-3. Extract with ethyl acetate (3×750 mL) and then combine and wash organics with water and then brine. Dry organics over sodium sulfate, filter and concentrate under vacuum. The title compound (24.7 g, 87%) was used for the next step reaction without further purification. LC-MS: m/z (ES) 286 (MH)+, 308 (MNa)+.

Workup

temperatureThe mixture was cooled to room temperature overnight
customthe temperature below 25° C.
extractionExtract with ethyl acetate (3×750 mL)
washwash organics with water
filtrationDry organics over sodium sulfate, filter
concentrationconcentrate under vacuum
customThe title compound (24.7 g, 87%) was used for the next step reaction without further purification

Sources & evidence

ORD record: ord-cbe14917a743449b8083197844af15d5
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748433B2

Reaction notes

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