(1,1'-Biphenyl)-4-sulphonyl chloride → [5-(Biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester

HRID 1696874Notes

Reaction equation

HRID 1696874 reaction equation
[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH2:19])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:21]1([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C>O1CCCC1>[C:1]([O:5][C:6](=[O:20])[CH2:7][O:8][C:9]1[C:18]2[CH2:17][CH2:16][CH2:15][CH:14]([NH:19][S:27]([C:24]3[CH:23]=[CH:22][C:21]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[CH:26][CH:25]=3)(=[O:29])=[O:28])[C:13]=2[CH:12]=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 74192(1,1'-Biphenyl)-4-sulphonyl chlorideHCID 81531DiisopropylethylamineHCID 59192558(5-Amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester

Product 1

HCID 59192584[5-(Biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (5-amino-5,6,7,8-tetrahydro-naphthalen-1-yloxy)-acetic acid tert-butyl ester (199 mg, 0.72 mmol) and biphenyl-4-sulfonyl chloride (217 mg, 0.86 mmol) in dry tetrahydrofuran (10 mL) was added diisopropylethylamine (186 mg, 1.44 mmol) at 0° C. The reaction mixture was stirred at room temperature for 12 hours, and then concentrated under reduced pressure. The residue was partitioned between water and ethyl acetate. The combined organic layers were washed with water, dried over sodium sulfate, and evaporated in vacuo. Column chromatography (silica gel, 100-200 mesh, 10-15% ethyl acetate in hexane) gave [5-(biphenyl-4-sulfonylamino)-5,6,7,8-tetrahydro-naphthalen-1-yloxy]-acetic acid tert-butyl ester. MS cald. for C28H31NO5S 493, obsd. 494 [(M+H)+].

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between water and ethyl acetate
  3. washThe combined organic layers were washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-9734bdf0a84b481eb6496c8de4a56b09
Source dataset
uspto-grants-2012_04
Patent number
US08163781B2

Reaction notes

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