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

HRID 1879356Notes

Reaction equation

HRID 1879356 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][CH:43]=[C:42]([NH2:46])[C:41]=1[NH2:47].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:46][C:42]1[CH:43]=[CH:44][CH:45]=[C:40]([O:39][CH3:38])[C:41]=1[NH2:47])[CH3:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 1842683-Methoxybenzene-1,2-diamineHCID 516892Sodium BicarbonateHCID 190283044-(((Benzyloxy)carbonyl)(methyl)amino)butanoic acid

Product 1

HCID 67380324[3-(2-Amino-3-methoxy-phenylcarbamoyl)-propyl]methyl-carbamic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.40 g 4-(benzyloxycarbonyl-methyl-amino)-butyric acid (obtained from 4-(methylamino)butyric acid and benzylchloroformate) in 25 mL THF were added 2.9 mL of DIPEA, 0.97 g of HOBt and 1.38 g EDC. After stirring for 5 min 0.80 g of 3-methoxy-benzene-1,2-diamine were added and the mixture was stirred for 3 h at rt. Sat. 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. additionwere 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-86ec1af97acc4b8b9e965c4e7e863553
Source dataset
uspto-grants-2012_11
Patent number
US08314253B2

Reaction notes

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