1-Hydroxybenzotriazole → HCID 22276506, compound

HRID 1063917Notes

Reaction equation

HRID 1063917 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2([CH2:33][C:34](O)=[O:35])[S:13](=[O:15])(=[O:14])[CH2:12][CH2:11][N:10]([C:16]([O:18][CH2:19][CH:20]3[C:32]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[C:26]4[C:21]3=[CH:22][CH:23]=[CH:24][CH:25]=4)=[O:17])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:43][NH2:44].ON1C2C=CC=CC=2N=N1>CN(C)C=O>[O:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[O:43][NH:44][C:34](=[O:35])[CH2:33][C:7]1([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)[S:13](=[O:14])(=[O:15])[CH2:12][CH2:11][N:10]([C:16]([O:18][CH2:19][CH:20]2[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=3[C:27]3[C:32]2=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:17])[CH2:9][CH2:8]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 22276782HCID 22276782, compound

Product 1

HCID 22276506HCID 22276506, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[7-(5-bromo-2-thienyl)-4-(9-fluorenylmethoxycarbonyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetic acid (400 mg), O-(2-tetrahydropyranyl)-hydroxylamine (95.2 mg) and 1-hydroxybenzotriazole (110 mg) in N,N-dimethylformamide (10 ml) was added WSCD-HCl (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) (156 mg) at room temperature. After being stirred at the same temperature overnight, the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate (30 ml) and the solution was washed successively with 5% aqueous citric acid solution, a saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate, and concentrated in vacuo. The residue was purified by SiO2 column chromatography (eluent; 1% MeOH in chloroform (CHCl3)) to afford N-(2-tetrahydropyranyloxy)-2-[7-(5-bromo-2-thienyl)-4-(9-fluorenylmethoxycarbonyl)-1,1-dioxoperhydro-1,4-thiazepin-7-yl]acetamide (313 mg) as an amorphous powder.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in ethyl acetate (30 ml)
  3. washthe solution was washed successively with 5% aqueous citric acid solution
  4. dry with materiala saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 column chromatography (eluent; 1% MeOH in chloroform (CHCl3))

Sources & evidence

ORD record
ord-98b4c2c8966e4b10abca2800338c5c1f
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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