Triphenylphosphine → HCID 54298263, compound

HRID 566731Notes

Reaction equation

HRID 566731 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)=[CH:12][NH:11][C:10](=[O:20])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(OC([NH:28][C@@H:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30]O)=O)(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C(Cl)Cl.CO>[NH2:28][C@@H:29]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:30][O:20][C:10]1[CH:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[C:13]([C:14]2[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=2)=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamateHCID 21266445HCID 21266445, compound

Product 1

HCID 54298263HCID 54298263, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 4-(3-methylphenyl)-5-(4-pyridyl)-1H-pyrid-2-one (12 mg, 0.05 mmole), (S)-2-tert-butoxycarbonylamino-3-phenylpropanol (15 mg, 0.06 mmole), triphenylphosphine (18 mg, 0.07 mmole), in methylene chloride (1 mL) at room temperature was added diethyl azodicarboxylate (12 mg, 0.07 mmol). When the reaction was complete (monitored by TLC), methanol was added (1 mL) and the reaction was concentrated and treated with 1 mL of 1:1 TFA/methanol for 30 minutes. The mixture was concentrated, neutralized with 1 drop conc NH4OH, and purified (SiO2, 10% methanol/methylene chloride) to give the title compound: MS (m/z): Calcd. C26H25N3O (M+): 395, found (M+H)+: 396.

Workup

  1. additionwas added (1 mL)
  2. concentrationthe reaction was concentrated
  3. additiontreated with 1 mL of 1:1 TFA/methanol for 30 minutes
  4. concentrationThe mixture was concentrated
  5. custompurified (SiO2, 10% methanol/methylene chloride)

Sources & evidence

ORD record
ord-3c3bbad8b5d74d9491e6088b53f30723
Source dataset
uspto-grants-2001_01
Patent number
US06174901B1

Reaction notes

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