Triphenylphosphine → HCID 54067761, compound

HRID 1789817Notes

Reaction equation

HRID 1789817 reaction equation
N(C(OC(C)C)=O)=NC([O:5][CH:6]([CH3:8])C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:34]1C=CC=C1CC(O)=O.[CH2:43]([O:45][C:46](=[O:67])[C:47]([CH2:52][C:53]1[CH:54]=[N:55][C:56]([NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[CH:57][CH:58]=1)([CH2:50]O)[CH2:48][CH3:49])[CH3:44]>C1COCC1>[CH2:43]([O:45][C:46](=[O:67])[C:47]([CH2:50][S:34][C:6](=[O:5])[CH3:8])([CH2:52][C:53]1[CH:54]=[N:55][C:56]([NH:59][C:60]([O:62][C:63]([CH3:66])([CH3:65])[CH3:64])=[O:61])=[CH:57][CH:58]=1)[CH2:48][CH3:49])[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 53715070HCID 53715070, compound

Product 1

HCID 54067761HCID 54067761, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (296 μL, 1.53 mmol) was added dropwise to a solution of triphenylphosphine (402 mg, 1.53 mmol) in THF (4 mL) at 0° C. under argon and the reaction was stirred for 30 min. A solution of thiolacetic acid (109 μL, 1.53 mmol) and 2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-2-hydroxymethyl-butyric acid ethyl ester (0.27 g, 0.77 mmol) in THF (2 mL) was added dropwise during 10 min. The reaction was stirred for 60 min. at 0° C. and then for 16 h at room temperature. Concentration under reduced pressure followed by chromathography (heptane/EtOAc, 10:1→1:1) gave 2-acetylsulfanylmethyl-2-(6-tert-butoxycarbonylamino-pyridin-3-ylmethyl)-butyric acid ethyl ester (193 mg, 61%).

Workup

  1. stirringThe reaction was stirred for 60 min. at 0° C.
  2. waitfor 16 h at room temperature
  3. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-c7bfad46cf2d45ad9426ac70adf14b9c
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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