Triphenylphosphine → 1-tert-Butoxycarbonyl-2(S)-(2-thioacetylethyl)-4-(1-naphthoyl)piperazine

HRID 1598482Notes

Reaction equation

HRID 1598482 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]([C:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH:50]=[CH:49][CH:48]=2)=[O:46])[CH2:41][C@@H:40]1[CH2:57][CH2:58]O)=[O:38])([CH3:35])([CH3:34])[CH3:33].[S:60]1C=C[CH:62]=[C:61]1CC(O)=O>O1CCCC1>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]([C:47]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH:50]=[CH:49][CH:48]=2)=[O:46])[CH2:41][C@@H:40]1[CH2:57][CH2:58][C:61](=[S:60])[CH3:62])=[O:38])([CH3:35])([CH3:33])[CH3:34]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 5462977Diethyl azodicarboxylateHCID 129668321-tert-Butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine

Product 1

HCID 867523771-tert-Butoxycarbonyl-2(S)-(2-thioacetylethyl)-4-(1-naphthoyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Triphenylphosphine (0.65 g, 2.5 mmol), in tetrahydrofuran (7 mL) was cooled to 0° C. and diethylazodicarboxylate (0.41 mL, 2.5 mmol) added. The reaction was stirred for 30 min, and 1-tert-butoxycarbonyl-2(S)-(2-hydroxyethyl)-4-naphthoylpiperazine (0.50 g, 1.3 mmol) and thiolacetic acid (0.18 mL, 2.5 mmol) were added in tetrahydrofuran (8 mL). After stirring at 20° C. for 16 h, the solvent was removed in vacuo and the residue chromatographed on silica with 30% ethyl acetate in hexane to give the title compound.

Workup

  1. stirringAfter stirring at 20° C. for 16 h
  2. customthe solvent was removed in vacuo
  3. customthe residue chromatographed on silica with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-e67bb3c1f2334920a04ac626a3be01e2
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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