1-Hydroxybenzotriazole → [3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester

HRID 220280

Reaktionsgleichung

Reaktionsgleichung von HRID 220280
[C:1]([O:5][C:6]([N:8]([CH3:15])[CH2:9][CH2:10][CH2:11][C:12]([OH:14])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.C1C=CC2N(O)N=NC=2C=1.[N+:35]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([NH2:44])[C:39]=1[NH2:45])([O-:37])=[O:36].C([O-])(O)=O.[Na+]>C(Cl)Cl.C(Cl)CCl>[C:1]([O:5][C:6](=[O:7])[N:8]([CH2:9][CH2:10][CH2:11][C:12](=[O:14])[NH:44][C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([N+:35]([O-:37])=[O:36])[C:39]=1[NH2:45])[CH3:15])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 43595253-Nitro-1,2-phenylenediamineHCID 106563904-{[(Tert-butoxy)carbonyl](methyl)amino}butanoic acid

Produkt 1

HCID 68412474[3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl esterAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 9 g of 4-(tert-butoxycarbonyl-methyl-amino)-butyric acid (prepared from 4-(methylamino)butyric acid and BOC anhydride) in 159 mL DCM were added 14.2 mL of DIPEA, 8 g of HOBt and 9.1 g of EDC. After stirring for 5 min 6.1 g of 3-nitro-benzene-1,2-diamine were added and the mixture was stirred for 4 days at rt. Saturated aq. NaHCO3 solution was added, the phases were separated and the organic phase washed with brine. The combined organic phases were dried over MgSO4, and concentrated in vacuo. Purification by CC using EtOAc/heptane 1/4 to 3/1 yielded 5.2 g of [3-(2-Amino-3-nitro-phenylcarbamoyl)-propyl]methyl-carbamic acid tert-butyl ester as orange foam.

Aufarbeitung

  1. additionwere added
  2. customthe phases were separated
  3. washthe organic phase washed with brine
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC

Quellen und Nachweise

ORD-Eintrag
ord-8d476292571949feb02165cc8d6ed4e2
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202885B2

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