1-Hydroxybenzotriazole → HCID 69586733, compound

HRID 1745415Notes

Reaction equation

HRID 1745415 reaction equation
[NH:1]([C:9]([CH3:11])=[O:10])[C@@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[C:34]([O:38][C:39]([C:41]1[C:49]2[CH2:48][CH2:47][O:46][CH:45]([CH2:50][NH2:51])[C:44]=2[S:43][C:42]=1[NH2:52])=[O:40])([CH3:37])([CH3:36])[CH3:35].C(N(CC)C(C)C)(C)C>ClCCl.CN(C)C=O>[C:34]([O:38][C:39]([C:41]1[C:49]2[CH2:48][CH2:47][O:46][CH:45]([CH2:50][NH:51][C:6](=[O:8])[C@H:2]([NH:1][C:9](=[O:10])[CH3:11])[CH:3]([CH3:4])[CH3:5])[C:44]=2[S:43][C:42]=1[NH2:52])=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 76475N-Acetyl-D-valineHCID 81531DiisopropylethylamineHCID 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 69586733HCID 69586733, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of Ac-D-Val-OH (0.17 g, 1.09 mmol) dissolved in dichloromethane (15 ml) was added N,N-dimethylformamide (1 ml), 1-hydroxybenzotriazole (0.15 g, 1.09 mmol) and 1-ethyl-3-(3-dimethylamino-propyl)carbodiimide hydrochloride (0.21 g, 1.09 mmol). The reaction mixture was stirred for 15 min. at room temperature at which time a solution of 2-amino-7-aminomethyl-4,7-dihydro-5H-thieno[2,3-c]pyran-3-carboxylic acid tert-butyl ester (0.31 g, 1.09 mmol) in dichloromethane (10 ml) was added followed by N,N-diisopropylethylamine (0.186 ml, 1.09 mmol). The resulting mixture was stirred over night at room temperature diluted with dichloromethane (10 ml) washed with 10% aqueous citric acid (20 ml), sodium hydrogencarbonate, dried (MgSO4), filtered and the solvent was evaporated in vacuo affording 415 mg (90%) of 7-((2-(R)-acetylamino-3-methyl-butyrylamino)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. washwashed with 10% aqueous citric acid (20 ml), sodium hydrogencarbonate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a1ea7c108e2543818a75a1bcd691aa99
Source dataset
uspto-grants-2006_03
Patent number
US07019026B1

Reaction notes

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