4,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchloride → HCID 57900508, compound

HRID 84601Notes

Reaction equation

HRID 84601 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH:12][CH2:13][CH2:14][O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:5]([O:7][CH3:8])=[O:6].CC1(C)[SiH2][SiH]=NC(C)(C)C1(C)C.[Na].[S:36]1[C:40]2[C:41]3[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=3[O:43][CH2:44][CH2:45][C:39]=2[CH:38]=[C:37]1[C:50](Cl)=[O:51]>C1COCC1>[Si:16]([O:15][CH2:14][CH2:13][N:12]([C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[Cl:1])[C:50]([C:37]1[S:36][C:40]2[C:41]3[CH:49]=[CH:48][CH:47]=[CH:46][C:42]=3[O:43][CH2:44][CH2:45][C:39]=2[CH:38]=1)=[O:51])([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 579001474,5-Dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonylchlorideHCID 66869046HCID 66869046, compoundHCID 131718990HCID 131718990, compound

Product 1

HCID 57900508HCID 57900508, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a soln. of methyl 3-chloro-4-(2-(tert-butyldimethylsilyloxy)ethylamino)benzoate (1.3 g 3.78 mmol) pretreated with 1M of sodium hexamethyldisilazine in THF (3.46 ml) in tetrahydrofuran (12.2 ml) was added at room temperature 4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carbonyl chloride (1.00 g, 3.79 mmol) portion-wise. The reaction mixture was stirred at room temperature under nitrogen for 1 hour. The reaction mixture was concentrated in vacuo and the residue taken into ethyl acetate and washed with water, then saline and dried (Na2SO4) to give 1.37 grams of crude methyl 4-(N-(2-(tert-butyldimethylsilyloxy)ethyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-3-chlorobenzoate. MS: (ESI+)=572.1

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washwashed with water
  3. dry with materialsaline and dried (Na2SO4)

Sources & evidence

ORD record
ord-2c9671a6f5414bf6919c132a10880ee1
Source dataset
uspto-grants-2014_09
Patent number
US08846762B2

Reaction notes

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