Triphenylphosphine → 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester

HRID 1789822Notes

Reaction equation

HRID 1789822 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:74])[C:47]([CH2:72]O)([CH3:71])[CH2:48][C:49]1[CH:50]=[N:51][C:52]([N:56]([C:64]([O:66][C:67]([CH3:70])([CH3:69])[CH3:68])=[O:65])[C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])=[C:53]([CH3:55])[CH:54]=1)[CH3:44]>C1COCC1>[CH2:43]([O:45][C:46](=[O:74])[C:47]([CH2:72][S:34][C:6](=[O:5])[CH3:8])([CH3:71])[CH2:48][C:49]1[CH:50]=[N:51][C:52]([N:56]([C:64]([O:66][C:67]([CH3:69])([CH3:70])[CH3:68])=[O:65])[C:57]([O:59][C:60]([CH3:61])([CH3:62])[CH3:63])=[O:58])=[C:53]([CH3:55])[CH:54]=1)[CH3:44]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 542575253-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-hydroxymethyl-2-methyl-propionic acid ethyl ester

Product 1

HCID 542605232-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl esterYield 145.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (755 μL, 3.91 mmol) was added dropwise to a solution of triphenylphosphine (1.026 g, 3.91 mmol) in THF (10 mL) at 0° C. and the reaction was stirred for 30 min. A solution of thiolacetic acid (279 μL, 3.91 mmol) and 3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-hydroxymethyl-2-methyl-propionic acid ethyl ester (885 mg, 1.96 mmol) in THF (5 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→1:3) gave impure 2-acetylsulfanylmethyl-3-(6-[N,N-bis(tert-butoxycarbonyl)amino]-5-methyl-pyridin-3-yl)-2-methyl-propionic acid ethyl ester (1.46 g)

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-aa19bb171de64621a59f5aa38227aad1
Source dataset
uspto-grants-2006_07
Patent number
US07071175B1

Reaction notes

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