Triphenylphosphine → 5-Chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide

HRID 1783414Notes

Reaction equation

HRID 1783414 reaction equation
[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]1[CH2:12][CH2:11][C:10]([F:14])([F:13])[CH2:9][C@@H:8]([NH:15][S:16]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)(=[O:18])=[O:17])[C:7]1=[O:25].[CH3:32][O:33][C:34]1[N:39]=[CH:38][C:37]([CH2:40]O)=[CH:36][CH:35]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[CH3:1][O:2][C:3]1[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:4]=1[CH2:5][N:6]1[CH2:12][CH2:11][C:10]([F:13])([F:14])[CH2:9][C@@H:8]([N:15]([CH2:40][C:37]2[CH:38]=[N:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=2)[S:16]([C:19]2[S:20][C:21]([Cl:24])=[CH:22][CH:23]=2)(=[O:17])=[O:18])[C:7]1=[O:25]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 12259941(6-Methoxypyridin-3-yl)methanolHCID 866107435-Chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide

Product 1

HCID 866107445-Chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-(6-methoxy-pyridin-3-ylmethyl)-amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-Chloro-thiophene-2-sulfonic acid [(R)-1-(2,4-dimethoxy-benzyl)-5,5-difluoro-2-oxo-azepan-3-yl]-amide (0.20 g, 0.40 mmol), (6-methoxy-pyridin-3-yl)-methanol (0.07 g, 0.48 mmol), triphenyl phosphine (0.22 g, 0.80 mmol) were dissolved in dry THF (15 ml) at 0-5° C. (ice-water bath) under an argon atmosphere followed by the dropwise addition of diisopropyl azodicarboxylate (0.16 ml, 0.80 mmol) in dry THF (1.5 ml). The reaction mixture was further stirred for 1 h at r.t. and then concentrated under reduced pressure. The crude oil was purified over silica gel (first: heptane-ethylacetate, 97:3-0:100; second: dichloromethane-methanol, 98:2-90:10): white solid 0.19 g (53%);

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe crude oil was purified over silica gel (first: heptane-ethylacetate, 97:3-0:100; second: dichloromethane-methanol, 98:2-90:10)

Sources & evidence

ORD record
ord-23f47b7a2fdc4ab9b979f6540c9278d9
Source dataset
uspto-grants-2009_03
Patent number
US07501406B2

Reaction notes

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