Triphenylphosphine → HCID 10168177, compound

HRID 1352239Notes

Reaction equation

HRID 1352239 reaction equation
N(C(OCC)=O)=NC(OCC)=O.C[O:14][C:15](=[O:45])[CH2:16][C:17]1[CH:22]=[C:21]([Br:23])[C:20]([O:24][C:25]2[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[C:28]([OH:34])=[CH:27][C:26]=2[C:35](=[O:43])[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[CH:37]=2)=[C:19]([Br:44])[CH:18]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:65][C:66](=[CH2:70])[CH2:67][CH2:68]O>C(Cl)Cl>[Br:44][C:19]1[CH:18]=[C:17]([CH2:16][C:15]([OH:14])=[O:45])[CH:22]=[C:21]([Br:23])[C:20]=1[O:24][C:25]1[CH:30]=[C:29]([CH:31]([CH3:33])[CH3:32])[C:28]([O:34][CH2:68][CH2:67][C:66]([CH3:70])=[CH2:65])=[CH:27][C:26]=1[C:35](=[O:43])[C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([CH3:42])[CH:37]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 129883-Methyl-3-buten-1-olHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 69512337HCID 69512337, compound

Product 1

HCID 10168177HCID 10168177, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of diethyl azodicarboxylate (42 mg, 0.24 mmol) in anhydrous CH2Cl2 (1 mL) was added over 15 min to an ice-cooled, stirred mixture of 3,5-dibromo-4-[4-hydroxy-5-isopropyl-2-(3-methylbenzoyl)phenoxy]phenylacetic acid methyl ester (70 mg, 0.12 mmol), PPh3 (63 mg, 0.24 mmol) and 3-methyl-3-buten-1-ol (24 μL, 0.24 mmol) in anhydrous CH2Cl2 (2 mL). The mixture was stirred at 0° C. for 12 h and 3 d at room temperature, and concentrated. The residue was dissolved in 30% NaOH/MeOH (2 mL) and heated at 40° C. for 12 h. The solution was allowed to cool, acidified with 1M HCl, concentrated and purified by HPLC to give the title compound. 1H NMR (CDCl3): δ 7.9–7.7 (m, 2H), 7.5 (s, 2H), 7.4–7.3 (m, 2H), 7.0(s, 1H), 6.3 (s, 1H), 4.8 (d, 2H), 4.1 (t, 2H), 3.6 (s, 2H), 3.3–3.2 (m, 1H), 2.5 (t, 2H), 2.4 (s, 3H), 1.8 (s, 3H), 1.1 (d, 6H). ESMS: m/z 629 (M−1).

Workup

  1. temperaturecooled
  2. stirringThe mixture was stirred at 0° C. for 12 h and 3 d at room temperature
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in 30% NaOH/MeOH (2 mL)
  5. temperatureto cool
  6. concentrationconcentrated
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-fda70926742148879eb69321fbb6e88d
Source dataset
uspto-grants-2007_05
Patent number
US07220752B2

Reaction notes

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