HCID 70008036, compound → HCID 18542151, compound

HRID 1267833Notes

Reaction equation

HRID 1267833 reaction equation
CC([O:5][C:6]([CH:8]1[C:13]([CH3:15])([CH3:14])[S:12][CH2:11][CH2:10][N:9]1[S:16]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[C:24]1[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][C:23]=1[O:22]2)(=[O:18])=[O:17])=[O:7])(C)C>FC(F)(F)C(O)=O>[CH:20]1[C:19]([S:16]([N:9]2[CH2:10][CH2:11][S:12][C:13]([CH3:15])([CH3:14])[CH:8]2[C:6]([OH:7])=[O:5])(=[O:18])=[O:17])=[CH:27][CH:26]=[C:25]2[C:21]=1[O:22][C:23]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][C:24]=12

Participants

3

Reactant 1

HCID 70008036HCID 70008036, compound

Product 1

HCID 18542151HCID 18542151, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The ester from Example 8 (0.184 g, 0.38 mmol) was diluted with trifluoroacetic acid (5 mL) and stirred at room temperature for overnight. The solution was poured over ice, and the resulting solid was collected by filtration and dried in vacuo to give the acid (0.133 g, 80%) as a cream colored solid. 1HNMR (DMSO-d6) δ 12.7 (bs, 1H), 7.8 (s, 1H), 7.7 (d, 1H), 7.5 (d, 1H), 4.3 (s, 1H), 3.9 (m, 1H), 3.6 (m, 1H), 2.9 (m, 3H), 2.8 (m, 2H), 2.3 (m, 1H), 1.8 (m, 2H), 1.7 (m, 2H), 1.5 (m, 2H), 1.49 (s, 3H), 1.2 (s, 3H) ppm.

Workup

  1. additionThe solution was poured over ice
  2. filtrationthe resulting solid was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cbde988124754f2c92b214044299d40e
Source dataset
uspto-grants-2003_04
Patent number
US06555535B2

Reaction notes

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