1-Hydroxybenzotriazole → [3-(2-Amino-4,5-dimethoxy-phenylcarbamoyl)-propyl]-methyl-carbamic acid benzyl ester

HRID 220239Notes

Reaction equation

HRID 220239 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH3:18])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[CH3:40][O:41][C:42]1[CH:43]=[C:44]([NH2:51])[C:45]([NH2:50])=[CH:46][C:47]=1[O:48][CH3:49].C([O-])(O)=O.[Na+]>C1COCC1.C(Cl)CCl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][CH2:14][C:15](=[O:17])[NH:50][C:45]1[CH:46]=[C:47]([O:48][CH3:49])[C:42]([O:41][CH3:40])=[CH:43][C:44]=1[NH2:51])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 130002194,5-Dimethoxybenzene-1,2-diamine--hydrogen chloride (1/2)HCID 190283044-(((Benzyloxy)carbonyl)(methyl)amino)butanoic acid

Product 1

HCID 68414218[3-(2-Amino-4,5-dimethoxy-phenylcarbamoyl)-propyl]-methyl-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.95 g 4-(benzyloxycarbonyl-methyl-amino)-butyric acid in 20 mL THF were added 3.3 mL of DIPEA, 0.61 g of HOBt and 0.86 g EDC. After stirring for 5 min 1.0 g of 4,5-dimethoxy-benzene-1,2-diamine dihydrochloride was added and the mixture was stirred at rt overnight. Saturated aq. NaHCO3 solution was added, the phases were separated and the organic phase was washed with brine. The combined organic phases were dried over MgSO4, and concentrated in vacuo.

Workup

  1. additionwas added
  2. customthe phases were separated
  3. washthe organic phase was washed with brine
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-22ca4ff8a7674726a83415621108f133
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Reaction notes

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