Triphenylphosphine → HCID 11568458, compound

HRID 2065448Notes

Reaction equation

HRID 2065448 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([NH:8][C:9]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:12]2)=[O:10])[CH2:4][CH2:3]1.[N:26]1[CH:31]=[CH:30][C:29](O)=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:20]1([S:17]([N:13]2[CH2:14][CH2:15][CH2:16][C@H:11]([C:9]([NH:8][CH:5]3[CH2:6][CH2:7][CH:2]([O:1][C:29]4[CH:30]=[CH:31][N:26]=[CH:27][CH:28]=4)[CH2:3][CH2:4]3)=[O:10])[CH2:12]2)(=[O:19])=[O:18])[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 178418642HCID 178418642, compoundHCID 178523813HCID 178523813, compound

Product 1

HCID 11568458HCID 11568458, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under a nitrogen atmosphere, to a mixture of (3S)—N-(trans-4-hydroxycyclohexyl)-1-(phenylsulfonyl)piperidine-3-carboxamide (25 mg, 0.068 mmol), 4-pyridinol (9.7 mg, 0.10 mmol), and triphenylphosphine (26.8 mg, 0.10 mmol) in tetrahydrofuran (0.5 mL) was added a solution of diethyl azodicarboxylate (16 μL, 0.10 mmol) in tetrahydrofuran (0.1 mL). The mixture was stirred at r.t. overnight. The product was purified with prep. HPLC. 1.9 mg product was obtained, yield: 6.3%. LCMS: m/z 444.2 (M+H)+; 887.2 (2M+Na)+.

Workup

  1. customThe product was purified with prep

Sources & evidence

ORD record
ord-339763f7c7c04ff8a66cb764b1f27e02
Source dataset
uspto-grants-2012_10
Patent number
US08288417B2

Reaction notes

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