Tributylphosphine → HCID 69285470, compound

HRID 2225256Notes

Reaction equation

HRID 2225256 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([NH:18][C:19](=[O:25])[O:20]C(C)(C)C)[CH2:14][C@H:13]1[CH2:26]O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1.C(P(C[CH2:45][CH2:46][CH3:47])CCCC)CCC.N(C(OC(C)C)=O)=N[C:50](OC(C)C)=O>C1C=CC=CC=1>[C:46]([N:18]([C@@H:15]1[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C@H:13]([CH2:26][N:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]2=[O:28])[CH2:14]1)[C:19](=[O:25])[OH:20])([CH3:45])([CH3:47])[CH3:50]

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68765914tert-butyl (1R,3R,4S)-4-benzyloxycarbonylamino-3-(hydroxymethyl)cyclohexylcarbamateHCID 178516071HCID 178516071, compound

Product 1

HCID 69285470HCID 69285470, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of tert-butyl(1R,3R,4S)-(4-benzyloxycarbonylamino-3-hydroxymethyl-cyclohexyl)carbamate (1.0 g), 2-hydroxypyridine (377 mg), and tributylphosphine (0.78 mL) in benzene (20 mL) was stirred at 0° C. and treated dropwise over 15 min with diisopropyl azodicarboxylate (0.8 g). The mixture was stirred overnight at rt and concentrated under vacuum. The residue was purified by radial preparative-layer chromatography to provide tert-butyl(1R,3S,4S)-(4-benzyloxycarbonylamino-3-((2-oxopyridin-1(2H)-yl)methyl)cyclohexyl)carbamic acid (1.06 g). MS found: (M+H)+=456.4.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified by radial preparative-layer chromatography

Sources & evidence

ORD record
ord-6c733a1a42e1457fbff95b76960c61d7
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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