Hydrochloric Acid → HCID 58079467, compound

HRID 444990Notes

Reaction equation

C[O:2][C:3](=[O:39])[C:4]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:5]=1.[OH-].[Na+].Cl.O>CO>[C:10]([O:9][C:7](=[O:8])[C:6]1[CH:5]=[C:4]([CH:16]=[CH:15][C:14]=1[O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[C:3]([OH:39])=[O:2])([CH3:13])([CH3:12])[CH3:11]

Participants

Conditions

Temperature: 0 °C

Procedure

4-(14-tert-Butoxycarbonyl-tetradecyloxy)-isophthalic acid 3-tert-butyl ester 1-methyl ester (381 mg, 0.69 mmol) was dissolved in methanol (10 ml). The solution was cooled to 0° C. and 4 N NaOH (1 ml) was added. The solution was allowed to warm to rt and more methanol (15 ml) was added. The reaction was stirred at rt for 30 min under N2, and at reflux for 2 h. The solution was cooled to 0° C. and 1 N HCl (1 ml) was added slowly. Water (25 ml) was added, and the solution was extracted with AcOEt (2×50 ml). The organic phases were pooled and washed with 1:1 water/sat. NaCl, dried over MgSO4, and concentrated under vacuum to yield an oily solid (326 mg, 89%)

Workup

temperatureto warm to rt
temperatureat reflux for 2 h
temperatureThe solution was cooled to 0° C.
extractionthe solution was extracted with AcOEt (2×50 ml)
washwashed with 1:1 water/
dry with materialNaCl, dried over MgSO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a1ba7e0abffa421fa64da2bfe3895bfc
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476228B2

Reaction notes

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