Triphenylphosphine → 4-Chloro-N-(6-methoxy-pyridin-3-ylmethyl)-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide

HRID 851975Notes

Reaction equation

HRID 851975 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[C:22]1[CH:23]=[CH:24][C:25](CO)=[N:26][CH:27]=1.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=N[C:51](OC(C)C)=[O:52]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:30][C:22]2[CH:27]=[N:26][C:25]([O:52][CH3:51])=[CH:24][CH:23]=2)[C@@H:12]2[CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C:13]2=[O:19])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69279554-Chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamideHCID 12214020(5-Methoxypyridin-2-yl)methanol

Product 1

HCID 671950924-Chloro-N-(6-methoxy-pyridin-3-ylmethyl)-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Chloro-N-((R)-2-oxo-azepan-3-yl)-benzenesulfonamide (0.04 g, 0.12 mmol), (5-Methoxy-pyridin-2-yl)-methanol (0.04 g, 030 mmol), triphenyl phosphine (0.08 g, 0.30 mmol) were dissolved in dry CH2Cl2 (6 ml) under an argon atmosphere followed by the dropwise addition of diisopropyl azodicarboxylate (60 mg, 0.30 ml) in dry CH2Cl2 (2 ml). The reaction mixture was further stirred overnight at r.t. and then concentrated under reduced pressure. The crude yellow oil was purified over silica gel (ethyl acetate/n-heptane 3:2): colorless gum 0.23 g (43%); MS: m/e=424.0 (MH+), 446.0 (MNa+).

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude yellow oil was purified over silica gel (ethyl acetate/n-heptane 3:2)

Sources & evidence

ORD record
ord-7355844456144f61aa10ea567e07defe
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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