1-Hydroxybenzotriazole → HCID 69585999, compound

HRID 1242071Notes

Reaction equation

HRID 1242071 reaction equation
[NH:1]([C:14]([CH3:16])=[O:15])[C@@H:2]([C:11]([OH:13])=O)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:39]([O:43][C:44]([C:46]1[C:54]2[CH2:53][CH2:52][O:51][CH:50]([CH2:55][NH2:56])[C:49]=2[S:48][C:47]=1[NH2:57])=[O:45])([CH3:42])([CH3:41])[CH3:40].C(N(CC)C(C)C)(C)C>ClCCl>[C:39]([O:43][C:44]([C:46]1[C:54]2[CH2:53][CH2:52][O:51][CH:50]([CH2:55][NH:56][C:11](=[O:13])[CH:2]([NH:1][C:14](=[O:15])[CH3:16])[CH2:3][C:4]3[CH:5]=[CH:6][C:7]([OH:10])=[CH:8][CH:9]=3)[C:49]=2[S:48][C:47]=1[NH2:57])=[O:45])([CH3:42])([CH3:40])[CH3:41]

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 853750N-Acetyl-D-tyrosineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 695860292-amino-7-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester

Product 1

HCID 69585999HCID 69585999, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a mixture of Ac-D-Tyr-OH (235 mg, 1.05 mmol) dissolved in dichloromethane (10 ml) was added 1-hydroxybenzotriazole (0.14 g, 1.05 mmol), 1-ethyl-3-(3-dimethylamino propyl)carbodiimide hydrochloride (0.20 g, 1.05 mmol) and the reaction mixture was stirred for 15 min at room temperature. 2-Amino-7-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.3 g, 1.05 mmol) dissolved in dichloromethane (10 ml) was added followed by N,N-diisopropyl-ethylamine (0.18 ml, 1.05 mmol). The resulting reaction mixture was stirred for 18 h at room temperature, diluted with dichloromethane (15 ml) was washed with 10% aqueous citric acid (25 ml), saturated sodium hydrogencarbonate, dried (MgSO4), filtered and the solvent removed in vacuo. The residue was purified by flash chromatography on silica gel (40 g) using ethyl acetate as eluant. Pure fractions were collected and the solvent evaporated in vacuo affording 304 mg (59%) of 7-((2-acetylamino-3-(4-hydroxy-phenyl)propionylamino)methyl)-2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester as an oil.

Workup

  1. additionwas added
  2. customThe resulting reaction mixture
  3. stirringwas stirred for 18 h at room temperature
  4. washwas washed with 10% aqueous citric acid (25 ml), saturated sodium hydrogencarbonate
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customThe residue was purified by flash chromatography on silica gel (40 g)
  9. customPure fractions were collected
  10. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3aef15abb971442dbaa3fc8534605092
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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