2-Phenylethanol → HCID 15956063, compound

HRID 1815592Notes

Reaction equation

HRID 1815592 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([OH:28])[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.[O:45]1[C:49]2[CH:50]=[CH:51][C:52]([S:54]([N:57]([CH2:82][CH:83]([CH3:85])[CH3:84])[CH2:58][C@@H:59]([OH:81])[C@@H:60]([NH:69][C:70](=[O:80])[O:71][C@@H:72]3[C@H:79]4[C@H:75]([O:76][CH2:77][CH2:78]4)[O:74][CH2:73]3)[CH2:61][C:62]3[CH:67]=[CH:66][C:65](O)=[CH:64][CH:63]=3)(=[O:56])=[O:55])=[CH:53][C:48]=2[O:47][CH2:46]1>C(Cl)Cl>[O:45]1[C:49]2[CH:50]=[CH:51][C:52]([S:54]([N:57]([CH2:82][CH:83]([CH3:85])[CH3:84])[CH2:58][C@@H:59]([OH:81])[C@@H:60]([NH:69][C:70](=[O:80])[O:71][C@@H:72]3[C@H:79]4[C@H:75]([O:76][CH2:77][CH2:78]4)[O:74][CH2:73]3)[CH2:61][C:62]3[CH:63]=[CH:64][C:65]([O:28][CH2:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[CH:66][CH:67]=3)(=[O:55])=[O:56])=[CH:53][C:48]=2[O:47][CH2:46]1

Participants

6

Reactant 4

HCID 60542-PhenylethanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 59997191(3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl) (isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate

Product 1

HCID 15956063HCID 15956063, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 66 mg (0.25 mmol) of triphenylphosphine and 30 μL (0.25 mmol) of phenethyl alcohol in 3 mL of anhydrous CH2Cl2 was added 58 mg (0.25 mmol) of di-tert-butyl azodicarboxylate. The resulting solution was stirred at RT for 5 minutes and was then treated with a solution of 50 mg (0.084 mmol) of (3R,3aS,6aR)hexahydrofuro[2,3-b]furan-3-yl (1S,2R)-3-[(1,3-benzodioxol-5-ylsulfonyl)(isobutyl)amino]-2-hydroxy-1-(4-hydroxybenzyl)propylcarbamate in 2 mL of CH2Cl2. After stirring at RT for 1.5 hours the solution was concentrated to dryness and the residue purified by flash chromatography (SiO2, 4:6 hexane/EtOAc) to give the desired product as a white foam in 72% yield. 1H NMR (CDCl3): 7.34-7.17 (m, 6H), 7.15 (s, 1H), 7.07 (d, 2H), 6.86 (d, 1H), 6.78 (d, 2H), 6.03 (s, 2H), 5.61 (d, 1H), 4.98 (m, 1H), 4.86 (d, 1H), 4.09 (t, 2H), 3.92 (m, 1H), 3.84-3.56 (m, 6H), 3.17-3.01 (m, 3H), 3.00-2.81 (m, 4H), 2.80-2.64 (m, 2H), 1.78 (m, 1H), 1.56 (m, 1H), 1.47 (m, 1H), 0.91 (d, 3H), 0.85 (d, 3H). MS(ESI): 697(M+H).

Workup

  1. stirringAfter stirring at RT for 1.5 hours the solution
  2. concentrationwas concentrated to dryness
  3. customthe residue purified by flash chromatography (SiO2, 4:6 hexane/EtOAc)

Sources & evidence

ORD record
ord-7b90811b740a4e628c00b27c9c67455f
Source dataset
uspto-grants-2005_04
Patent number
US06878728B1

Reaction notes

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