Anisole → HCID 67178457, compound

HRID 587621Notes

Reaction equation

HRID 587621 reaction equation
C1(OC)C=CC=CC=1.COC1C=CC(C[O:16][C:17](=[O:64])[CH:18]([NH:33][C:34]([NH:36][CH:37]([C:52]([O:54]CC2C=CC(OC)=CC=2)=[O:53])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43](=[O:51])[C:44]2[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=2)=[O:35])[CH2:19][CH2:20][C:21]([O:23]CC2C=CC(OC)=CC=2)=[O:22])=CC=1>C(O)(C(F)(F)F)=O>[C:52]([CH:37]([NH:36][C:34](=[O:35])[NH:33][CH:18]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[C:17]([OH:64])=[O:16])[CH2:38][CH2:39][CH2:40][CH2:41][NH:42][C:43](=[O:51])[C:44]1[CH:45]=[CH:46][C:47]([F:50])=[CH:48][CH:49]=1)([OH:54])=[O:53]

Participants

4

Reactant 2

HCID 7519AnisoleHCID 67229569HCID 67229569, compound

Product 1

HCID 67178457HCID 67178457, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3% anisole in TFA (15 mL) was added to 5 (0.081 g, 0.1 mmol) at 0° C. The mixture was stirred at room temperature for 20 min then concentrated on a rotary evaporator. The crude material was purified by HPLC (Econosil C18 10 μm, 250×10 mm, H2O/CH3CN/TFA (75/25/0.1), 4 mL/min, with purified 6 eluting at about 9 min) to afford 0.035 g (79%) of 6. 1H NMR (400 MHz, D2O) δ 7.66-7.69 (m, 2H), 7.11-7.16 (m, 2H), 4.12-4.19 (m, 2H), 3.28-3.31 (m, 2H), 2.39-2.43 (m, 2H), 2.07-2.09 (m, 1H), 1.79-1.90 (m, 2H), 1.55-1.69 (m, 3H), 1.39-1.40 (m, 2H). ESI-Mass calcd for C19H24FN3O8Na [M+Na]+ 464.1, found 464.4. FAB-HRMS calcd for C19H25FN3O8 [M+H]+ 442.1626, found 442.1646.

Workup

  1. concentrationthen concentrated on a rotary evaporator
  2. customThe crude material was purified by HPLC (Econosil C18 10 μm, 250×10 mm, H2O/CH3CN/TFA (75/25/0.1), 4 mL/min, with purified 6 eluting at about 9 min)

Sources & evidence

ORD record
ord-a92d9388709d4ac087853476277637e9
Source dataset
uspto-grants-2016_01
Patent number
US09226981B2

Reaction notes

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