1,2-Dichloroethane → [2-(2-Amino-3-methoxy-phenylcarbamoyl)-ethyl]-methyl-carbamic acid tert.-butyl ester

HRID 220250

Reaction equation

HRID 220250 reaction equation
[C:1]([O:5][C:6](C(NC)(C)C(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[CH2:16][N:17]([CH:21](C)C)C(C)C.C1C=CC2N([OH:33])N=NC=2C=1.[CH3:34][O:35][C:36]1[CH:41]=[CH:40][CH:39]=[C:38]([NH2:42])[C:37]=1[NH2:43].[CH2:44](Cl)[CH2:45]Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([O:5][C:6](=[O:7])[N:17]([CH2:21][CH2:44][C:45](=[O:33])[NH:42][C:38]1[CH:39]=[CH:40][CH:41]=[C:36]([O:35][CH3:34])[C:37]=1[NH2:43])[CH3:16])([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1842683-Methoxybenzene-1,2-diamineHCID 86641926Tert.-butoxycarbonyl-methylamino-propanoic acid

Product 1

HCID 68411798[2-(2-Amino-3-methoxy-phenylcarbamoyl)-ethyl]-methyl-carbamic acid tert.-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.35 g of tert.-butoxycarbonyl-methylamino-propanoic acid in 50 mL DCM were added 3.4 mL of DIPEA, 81 mg of DMAP, 1.0 g of HOBt, 1.5 g of EDC and 0.91 g of 3-methoxybenzene-1,2-diamine. The resulting mixture was stirred at rt for 3 h and then quenched with water. The organic phase was washed with sat. aq. NaHCO3, dried over MgSO4 and concentrated on vacuo to yield 2.9 g of [2-(2-amino-3-methoxy-phenylcarbamoyl)-ethyl]-methyl-carbamic acid tert.-butyl ester as brown oil.

Workup

  1. customquenched with water
  2. washThe organic phase was washed with sat. aq. NaHCO3
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated on vacuo

Sources & evidence

ORD record
ord-39e36709953048d28651a2f8cb4122a3
Source dataset
uspto-grants-2012_06
Patent number
US08202885B2

Linked notes

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