Sodium Azide → Benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate

HRID 1696329노트

반응식

HRID 1696329 반응식
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[O:4].[N-:21]=[N+:22]=[N-:23].[Na+]>>[N:21]([CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH:7]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:6]1)=[O:4])=[N+:22]=[N-:23]

참가 물질

3

반응물 2

HCID 33557Sodium AzideHCID 66844936Benzyl 4-(2-chloroacetyl)morpholine-2-carboxylate

생성물 1

HCID 86614022Benzyl 4-(2-azidoacetyl)morpholine-2-carboxylate수율 86.4%

실험 절차

In a 25-mL round-bottom flask, the benzyl 4-(2-chloroacetyl)morpholine-2-carboxylate (0.262 g, 0.88 mmol) was dissolved in dmf (4 mL). Sodium azide (0.066 g, 1.0 mmol) was added, and the flask was placed in a 60 deg oil bath overnight. The reaction was concentrated, and the residue was taken up in 80% ether-hexane (60 mL) and the organic layer was extracted with dilute sodium bicarbonate (2×7 mL) then with saturated brine (7 mL), then was dried over magnesium sulfate, filtered, and concentrated. The residue was purified through silica gel (50 mL) which had been deactivated with TEA (5 mL) using 60% EtOAc-hexane to afford the title compound (230 mg, 0.76 mmol). MS m/z 305 (M+1).

후처리

  1. customwas placed in a 60 deg
  2. customovernight
  3. concentrationThe reaction was concentrated
  4. extractionthe organic layer was extracted with dilute sodium bicarbonate (2×7 mL)
  5. dry with materialwith saturated brine (7 mL), then was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified through silica gel (50 mL) which

출처 및 근거

ORD 기록
ord-f1681d93df93470fb909076ba086c520
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08163766B2

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