1-Hydroxybenzotriazole → HCID 86006107, compound

HRID 1694696Notes

Reaction equation

HRID 1694696 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[CH2:28][C:29]([OH:31])=O)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.Cl.[CH3:33][NH:34][O:35][CH3:36].ON1C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>CN(C=O)C>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=1[CH2:28][C:29]([N:34]([O:35][CH3:36])[CH3:33])=[O:31])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 3337903HCID 3337903, compound

Product 1

HCID 86006107HCID 86006107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(3-Dimethylaminopropyl)3-ethylcarbodiimide hydrochloride (8.6 g) was added to a solution of (2-benzyloxy-5-chlorophenyl)-acetic acid (10.6 g), N,O-dimethylhydroxylamine hydrochloride (4.4 g), 1-hydroxybenzotriazole (6.9 g) and N,N-diisopropylethylamine (20 ml) in DMF (150 ml) and the mixture stirred at RT for 16 h, then partitioned between ethylacetate and water. The organics were washed with 2M hydrochloric acid, water, dried, and evaporated under reduced pressure. Yield 12.2 g

Workup

  1. custompartitioned between ethylacetate and water
  2. washThe organics were washed with 2M hydrochloric acid, water
  3. customdried
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-f31c5b67e0f2429897c1a71b3d7e4930
Source dataset
uspto-grants-2012_04
Patent number
US08158820B2

Reaction notes

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