Triphenylphosphine → HCID 67255038, compound

HRID 1830745Notes

Reaction equation

HRID 1830745 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:36][N:37]([CH3:42])[CH2:38][CH2:39][CH2:40]O.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[O:15][CH2:40][CH2:39][CH2:38][N:37]([CH3:42])[CH3:36])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 766463-(Dimethylamino)-1-propanolHCID 4935484HCID 4935484, compound

Product 1

HCID 67255038HCID 67255038, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred, cooled (about 0° C.) solution of (2-hydroxy-5-methyl-phenyl)-carbamic acid tert-butyl ester (447 mg, 2.0 mmol), triphenyl phosphine (525 mg, 2.0 mmol), and 3-(dimethylamino)-1-propanol (237 μL, 2.0 mmol) in dry tetrahydrofuran (5 mL) was added diisopropyl azodicarboxylate (394 μL, 2.0 mmol) in 1 mL of tetrahydrofuran). After stirring for 12 hours, the reaction was diluted with 30 mL of ethyl acetate and washed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL), then dried (MgSO4), and filtered. The filtered solution was concentrated under reduced pressure to provide the desired crude product.

Workup

  1. washwashed with 30 mL of 10% aqueous sodium carbonate (2×30 mL), brine (1×30 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtered solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-147b135dbe414b53809b0ee29a83f562
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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