Triphosgene → HCID 58091390, 화합물

HRID 2045691노트

반응식

HRID 2045691 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 58091390HCID 58091390, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-864feaddfa054d1984467162635da692
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08591878B2

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