1-Hydroxybenzotriazole → HCID 86588741, compound

HRID 1063931Notes

Reaction equation

HRID 1063931 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]([C@:14]3([CH2:29][C:30](O)=[O:31])[S:20](=[O:22])(=[O:21])[CH2:19][CH2:18][N:17]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH2:16][CH2:15]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)[CH3:2].[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:39][NH2:40].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O.C(Cl)(Cl)Cl.CO.C(OCC)(=O)C>[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:39][NH:40][C:30](=[O:31])[CH2:29][C@@:14]1([C:12]2[S:13][C:9]([C:6]3[CH:7]=[CH:8][C:3]([CH2:1][CH3:2])=[CH:4][CH:5]=3)=[CH:10][CH:11]=2)[S:20](=[O:21])(=[O:22])[CH2:19][CH2:18][N:17]([S:23]([CH2:26][CH2:27][CH3:28])(=[O:25])=[O:24])[CH2:16][CH2:15]1

Participants

9

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 5142091O-(Tetrahydropyran-2-yl)hydroxylamineHCID 69746573HCID 69746573, compound

Product 1

HCID 86588741HCID 86588741, compoundYield 91.7%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-propanesulfonyl-1,4-thiazepin-7-yl]acetic acid (3.95 g) in dimethylformamide (DMF) (40 ml) were added N-(2-tetrahydropyranyloxy)amine (1.30 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC; 1.82 g), and 1-hydroxybenzotriazole (HOBt; 1.28 g) at 0° C. The resulting mixture was stirred for 3 hours at room temperature. Ethyl acetate (500 ml) was added and the solution was washed with water (300 ml×3), saturated sodium bicarbonate, and brine, dried over magnesium sulfate, and evaporated to give a pale yellow solid. Silica gel column chromatography (eluent: 0 to 0.3% methanol in chloroform) afforded N-(2-tetrahydropyranyloxy)-2-[(S)-7-[5-(4-ethylphenyl)-2-thienyl]-1,1-dioxoperhydro-4-propanesulfonyl-1,4-thiazepin-7-yl]acetamide (4.34 g) as a pale yellow solid.

Workup

  1. washthe solution was washed with water (300 ml×3), saturated sodium bicarbonate, and brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated
  4. customto give a pale yellow solid

Sources & evidence

ORD record
ord-da5dcf7539344a14928dcb314aa95321
Source dataset
uspto-grants-2005_11
Patent number
US06967197B2

Reaction notes

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