Triphenylphosphine → HCID 10339099, compound

HRID 1827867Notes

Reaction equation

HRID 1827867 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:20])=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[N:16][C:15]([C:18]#[N:19])=[CH:14][N:13]=2)=[O:10])[CH:7]=1.[CH:21]1(O)[CH2:26][CH2:25][CH2:24][CH:23]=[CH:22]1.C(OC(N=NC(OC(C)(C)C)=O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:20][CH:26]2[CH2:25][CH2:24][CH2:23][CH:22]=[CH:21]2)=[C:6]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[N:16][C:15]([C:18]#[N:19])=[CH:14][N:13]=2)=[O:10])[CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 131982-Cyclohexen-1-OLHCID 97268Di-tert-butyl azodicarboxylateHCID 135724449660851-46-7

Product 1

HCID 10339099HCID 10339099, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of Example 1F (28.9 mg, 0.10 mmol), 2-cyclohexen-1-ol (9.8 mg, 0.10 mmol), di-tert-butylazocarboxylate (34.5 mg, 0.15 mmol), triphenylphosphine on polystyrene (3 mmol/g, 50 mg, 0.15 mmol) and THF (2 mL) in a capped 4-mL vial was shaken at room-temperature overnight and filtered. The resin was washed twice with THF (1 mL each) and the combined THF washes were concentrated. The concentrate was purified by preparative HPLC with acetonitrile/water containing 0.1% TFA to provide 4.4 mg (12%) of the desired product. MS (ESI(−)) m/z 368 (M−H)−; 1H NMR (500 MHz, DMSO-d6) δ 10.99 (s, 1H), 10.05 (br s, 1H), 8.92 (s, 1H), 8.73 (s, 1H), 8.27 (d, J=2.5 Hz, 1H), 7.17 (d, J=8.7 Hz, 1H), 7.06 (dd, J=8.9, 2.7 Hz, 1H), 6.01–6.08 (m, 1H), 5.85–5.92 (m, 1H), 4.97–5.04 (m, 1H), 1.89–2.19 (m, 3H), 1.73–1.85 (m, 2H), 1.56–1.68 (m, 1H).

Workup

  1. filtrationfiltered
  2. washThe resin was washed twice with THF (1 mL each)
  3. concentrationthe combined THF washes were concentrated
  4. customThe concentrate was purified by preparative HPLC with acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-1a7fed162a6b4f5e82578fee4277f58a
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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