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

HRID 220280

反応式

HRID 220280 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8d476292571949feb02165cc8d6ed4e2
出典データセット
uspto-grants-2012_06
特許番号
US08202885B2

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