1-Hydroxybenzotriazole → 1-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide

HRID 2269318Notes

Reaction equation

HRID 2269318 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:18]2[CH2:23][CH:22]([O:24][CH3:25])[CH2:21][CH2:20][CH:19]2[C:26](O)=[O:27])(=[O:17])=[O:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.Cl.[CH2:40]([O:43][NH2:44])[CH:41]=[CH2:42].C(N(C(C)C)CC)(C)C.CCN=C=NCCCN(C)C.Cl>C(OCC)(=O)C.C(Cl)Cl>[CH2:40]([O:43][NH:44][C:26]([CH:19]1[CH2:20][CH2:21][CH:22]([O:24][CH3:25])[CH2:23][N:18]1[S:15]([C:12]1[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:10][CH:11]=1)(=[O:16])=[O:17])=[O:27])[CH:41]=[CH2:42]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3084724O-Allylhydroxylamine hydrochlorideHCID 183337301-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid

Product 1

HCID 544425521-(4-Benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amideYield 102.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid (0.077 g, 0.19 mmol), HOBT (0.044 g, 0.29 mmol), O-allylhydroxylamine hydrochloride (0.043 g, 0.29 mmol), di-isopropylethylamine (0.066 mL, 0.38 mmol) and CH2Cl2 (2 mL) was treated with EDCl (0.056 g, 0.29 mmol). After stirring for 24 h at room temperature, the mixture was diluted with ethyl acetate, washed with 1M HCl, saturated aqueous NaHCO3, dried over Na2SO4, filtered and concentrated in vacuo, affording 1-(4-benzyloxy-benzenesulfonyl)-5-methoxy-piperidine-2-carboxylic acid allyloxy-amide (0.090 g, 100%) as a colorless syrup:

Workup

  1. washwashed with 1M HCl, saturated aqueous NaHCO3
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81bd23a758c640d184d29f6404d11fe4
Source dataset
uspto-grants-2001_12
Patent number
US06329397B1

Reaction notes

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