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1-Hydroxybenzotriazole → [3-(2-Amino-3,6-dimethoxy-phenylcarbamoyl)-propyl]-methyl-carbamic acid benzyl ester

HRID 453711
Notes
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Reaction equation

HRID 453711 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.[CH3:38][O:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[C:42]([NH2:48])[C:41]=1[NH2:49]>C(Cl)Cl.CN(C1C=CN=CC=1)C.C(Cl)CCl>[CH2:1]([O:8][C:9](=[O:10])[N:11]([CH2:12][CH2:13][CH2:14][C:15](=[O:17])[NH:48][C:42]1[C:43]([O:46][CH3:47])=[CH:44][CH:45]=[C:40]([O:39][CH3:38])[C:41]=1[NH2:49])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 116296603,6-Dimethoxybenzene-1,2-diamineHCID 190283044-(((Benzyloxy)carbonyl)(methyl)amino)butanoic acid

Product 1

HCID 66899923[3-(2-Amino-3,6-dimethoxy-phenylcarbamoyl)-propyl]-methyl-carbamic acid benzyl ester

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 111,2-DichloroethaneSolvent
HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3.1 g of 4-(benzyloxycarbonyl-methyl-amino)-butyric acid in 80 mL DCM were added 6.5 mL of DIPEA, 1.8 g of HOBt, 2.6 g of EDC and 154 mg of DMAP. After stirring for 10 min, 2.1 g of 3,6-dimethoxy-benzene-1,2-diamine, dissolved in 20 mL DCM, were added and the mixture was stirred at rt overnight. The reaction was quenched with sat. aq. NaHCO3, the phases were separated and the organic phase was washed with brine, dried over MgSO4 and concentrated in vacuo to yield the crude title compound as black oil.

Workup

  1. additionwere added
  2. stirringthe mixture was stirred at rt overnight
  3. customThe reaction was quenched with sat. aq. NaHCO3
  4. customthe phases were separated
  5. washthe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-912d15ff2dd44d01bcd55d968668a820
Source dataset
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08492555B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes