Triphosgene → HCID 58091390、化合物

HRID 2045691ノート

反応式

HRID 2045691 の反応式
[C:1]([O-])(O)=[O:2].[Na+].Cl.[NH2:7][C@@H:8]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:9]([O:11][CH3:12])=[O:10].ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[CH:13]1([C@H:8]([N:7]=[C:1]=[O:2])[C:9]([O:11][CH3:12])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

5

反応物 3

HCID 94429TriphosgeneHCID 516892Sodium BicarbonateHCID 17747951(S)-Methyl 2-amino-2-cyclohexylacetate hydrochloride

生成物 1

HCID 58091390HCID 58091390、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A 500 mL round-bottom flask was charged with saturated NaHCO3 (80 mL) and DCM (80 ml) and cooled in an ice bath with vigorous stirring. Methyl (2S)-amino(cyclohexyl)acetate hydrochloride (4.0 g, 19.26 mmol) was added followed by triphosgene (1.886 g, 6.36 mmol). The contents of the reaction flask were stirred for 1 hr with cooling, then poured into a reparatory funnel. The layers were separated, and the aqueous layers were extracted with 20 mL DCM. The combined organic portions were dried with anhydrous MgSO4, filtered and evaporated to give the title compound as a colorless oil. 1H NMR (CDCl3): δ 3.90 (d, J 4, 1H), 3.81 (s, 3H), 1.88-1.83 (m, 1H), 1.79-1.76 (m, 2H), 1.69-1.62 (m, 2H), 1.54-1.48 (m, 1H), 1.29-1.11 (m, 5H) ppm.

後処理

  1. temperaturecooled in an ice bath with vigorous stirring
  2. temperaturewith cooling
  3. additionpoured into a reparatory funnel
  4. customThe layers were separated
  5. extractionthe aqueous layers were extracted with 20 mL DCM
  6. dry with materialThe combined organic portions were dried with anhydrous MgSO4
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-864feaddfa054d1984467162635da692
出典データセット
uspto-grants-2013_11
特許番号
US08591878B2

反応ノート

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