HCID 86618754, compound → HCID 71082821, compound

HRID 1525819Notes

Reaction equation

HRID 1525819 reaction equation
C(OC([NH:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])=O)(C)(C)C.[OH:20][CH2:21][CH2:22][N:23]1[C:28](=[O:29])[CH2:27][CH2:26][CH:25]([N:30]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:40])[C:24]1=[O:41]>C(O)(C(F)(F)F)=O.C(Cl)Cl.C(Cl)Cl>[NH2:8][C@@H:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11].[OH:20][CH2:21][CH2:22][N:23]1[C:28](=[O:29])[CH2:27][CH2:26][CH:25]([N:30]2[C:31](=[O:40])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]2=[O:39])[C:24]1=[O:41]

Participants

4

Reactant 1

HCID 86618754HCID 86618754, compound

Product 1

HCID 71082821HCID 71082821, compoundYield 63.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

2-(1-(2-hydroxyethyl)-2,6-dioxopiperidin-3-yl)isoindolin-1,3-dione (S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoate (100 mg) was dissolved in 25% TFA/DCM (10 mL) and stirred on a magnetic stirrer at room temperature. The mixture was allowed to react for 4 hrs. DCM and most of TFA were removed by rotary evaporation in vacuo. The foam obtained was dissolved in DCM (50 mL). The mixture was washed with saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, and filtered. 52 mg of a solid was obtained after drying in vacuo. 1H NMR (CDCl3, ppm) δ 7.80-7.90 (m, 2H), 7.70-7.80 (m, 2H), 7.10-7.35 (m, 5H), 4.95-5.12 (m, 1H), 4.35-4.45 (m, 1H), 4.15-4.25 (m, 2H), 4.00-4.15 (m, 1H), 3.65-3.72 (m, 1H), 2.95-3.10 (m, 2H), 2.75-2.90 (m, 3H), 2.12-2.20 (m, 1H).

Workup

  1. customto react for 4 hrs
  2. customDCM and most of TFA were removed by rotary evaporation in vacuo
  3. customThe foam obtained
  4. washThe mixture was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-c3a712fdc9e0466fa6bbba438198800a
Source dataset
uspto-grants-2015_07
Patent number
US09085563B2

Reaction notes

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