Triphenylphosphine → methyl (2S)-3-[4-[1-(benzyloxycarbonyl)-4-piperidyloxy]phenyl]-2-(t-butoxycarbonylamino)propionate

HRID 747756Notes

Reaction equation

HRID 747756 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[C:18]([O:22][C:23]([NH:25][C@@H:26]([CH2:31][C:32]1[CH:37]=[CH:36][C:35](O)=[CH:34][CH:33]=1)[C:27]([O:29][CH3:30])=[O:28])=[O:24])([CH3:21])([CH3:20])[CH3:19].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1.C(OCC)(=O)C>[CH2:11]([O:10][C:8]([N:5]1[CH2:4][CH2:3][CH:2]([O:1][C:35]2[CH:34]=[CH:33][C:32]([CH2:31][C@H:26]([NH:25][C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[C:27]([O:29][CH3:30])=[O:28])=[CH:37][CH:36]=2)[CH2:7][CH2:6]1)=[O:9])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2794620Benzyl 4-Hydroxy-1-piperidinecarboxylateHCID 7019130Boc-Tyr-OMe

Product 1

HCID 86760707methyl (2S)-3-[4-[1-(benzyloxycarbonyl)-4-piperidyloxy]phenyl]-2-(t-butoxycarbonylamino)propionate

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

18.9 g (86.2 mmol) of benzyl 4-hydroxypiperidine-1-carboxylate, 25.4 g (86.2 mmol) of methyl (2S)-2-(t-butoxycarbonylamino)-3-(4-hydroxyphenyl)propionate and 27.1 g (103.4 mmol) of triphenylphosphine were dissolved in 500 ml of tetrahydrofuran. 37.5 g (86.2 mmol) of diethyl azodicarboxylate was added to the solution at room temperature, and they were stirred for 15 hours. After the isolation treatment with ethyl acetate as the extractant in the same manner as that of step 1 in Example 1, the crude product was obtained, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. customwhich was purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-7c4ccc47302e4f82b21b8218bb989a3e
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

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