1,2-Dichloroethane → (R)-tert-butyl 2-amino-1-cyclopropyl-2-oxoethylcarbamate

HRID 84847ノート

反応式

HRID 84847 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]1[CH2:15][CH2:14]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=[N:26]C=2C=1.N.CO>CN(C=O)C.O.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH:13]1[CH2:15][CH2:14]1)[C:10]([NH2:26])=[O:11])([CH3:4])([CH3:3])[CH3:2]

参加物

9

反応物 5

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 887MethanolHCID 757711-HydroxybenzotriazoleHCID 7146275(R)-2-((tert-Butoxycarbonyl)amino)-2-cyclopropylacetic acid

生成物 1

HCID 67776181(R)-tert-butyl 2-amino-1-cyclopropyl-2-oxoethylcarbamate

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (R)-2-(tert-butoxycarbonylamino)-2-cyclopropylacetic acid (430 mg, 2 mmol) in DMF (6 ml) was added EDC (461 mg, 2.4 mmol) and HOBt. H2O (367 mg, 2.4 mmol) at room temperature, 20 min later, it was added ammonia in MeOH (7N, 0.6 mL, 4 mmol) at room temperature. After stirring for 30 min, it was diluted with water and EtOAc, organic layer was separated and washed with Sat. NaHCO3, brine, dried and concentrated to give (R)-tert-butyl-2-amino-1-cyclopropyl-2-oxoethylcarbamate (330 mg) as crude oil, which was treated with 4N HCl in Dioxane (2 mL). 30 min later, it was concentrated to give (R)-2-amino-2-cyclopropylacetamide hydrochloride salt.

後処理

  1. customwas separated
  2. washwashed with Sat. NaHCO3, brine
  3. customdried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-4bb620dcfda446d39180ec362c5c3cac
出典データセット
uspto-grants-2014_09
特許番号
US08846928B2

反応ノート

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