1-Hydroxybenzotriazole → HCID 54355146, compound

HRID 650672Notes

Reaction equation

HRID 650672 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([NH:14][S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])(=[O:17])=[O:16])[C:11](O)=[O:12])=[O:7])(C)(C)C.[C:27]([O:31][C:32](=[O:43])[NH:33][CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([NH2:42])=[CH:38][CH:37]=1)([CH3:30])([CH3:29])[CH3:28].[CH:44]1[CH:45]=[CH:46][C:47]2N(O)N=N[C:48]=2[CH:49]=1.Cl.C(N=C=N)C>CN(C=O)C>[CH2:1]([O:5][C:6](=[O:7])[NH:8][CH2:9][CH:10]([C:11](=[O:12])[NH:42][C:39]1[CH:40]=[CH:41][C:36]([CH2:35][CH2:34][NH:33][C:32]([O:31][C:27]([CH3:30])([CH3:28])[CH3:29])=[O:43])=[CH:37][CH:38]=1)[NH:14][S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])(=[O:17])=[O:16])[C:48]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:49]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 382207Tert-butyl 4-aminophenethylcarbamateHCID 21712805HCID 21712805, compoundHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 54355146HCID 54355146, compoundYield 44.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 3-tert-Butoxycarbonylamino-2-(2,4,6-trimethyl-benzenesulfonylamino)-propionic acid (200 mg, 0.51 mmol), [2-(4-Amino-phenyl)-ethyl]-carbamic acid tert-butyl ester (130 mg, 0.55 mmol), HOBT (82 mg, 0.612 mmol) in DMF (25 mL), was added 1-(3-dimethylamino) propyl)-3-ethylcarbodiimide hydrochloride (118 mg, 0.612 mmol). The reaction was stirred overnight at room temperature. Insoluble particles were removed by filtration and the solvent was evaporated. Purification of the residue on silica gel (1:4 hexane:EtOAc) gave 144 mg (42%) of pure [2-[4-(2-tert-Butoxycarbonylamino-ethyl)-phenylcarbamoyl]-2-(2,4,6-trimethyl-benzenesulfonylamino)-ethyl]-carbamic acid benzyl ester (Y-2).

Workup

  1. customInsoluble particles were removed by filtration
  2. customthe solvent was evaporated
  3. customPurification of the residue on silica gel (1:4 hexane:EtOAc)

Sources & evidence

ORD record
ord-a0383c4530ed4541b27a2164bbc101da
Source dataset
uspto-grants-2001_08
Patent number
US06274620B1

Reaction notes

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