Sodium Azide → Tert-butyl 2-azidobenzylcarbamate

HRID 1253895노트

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HRID 1253895 반응식
[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])([CH3:4])([CH3:3])[CH3:2].N([O-])=O.[Na+].[N-:21]=[N+:22]=[N-].[Na+]>C(O)(=O)C.O>[C:1]([O:5][C:6](=[O:16])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]=[N+:21]=[N-:22])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 3

HCID 33557Sodium AzideHCID 4409487tert-butyl N-[(2-aminophenyl)methyl]carbamateHCID 23668193Sodium Nitrite

생성물 1

HCID 59176460Tert-butyl 2-azidobenzylcarbamate수율 96%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매2회

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온도
0 °C

실험 절차

To a solution of (2-amino-benzyl)-carbamic acid tert-butyl ester [prepared from 2-aminobenzylamine and di-tert-butyl dicarbonate], (100 mg, 0.45 mmol) in acetic acid (2.46 mL), was added water (26 mL). Reaction mixture was cooled to 0° C. and a solution of sodium nitrite (62 mg, 0.9 mmol) in water (4.3 ml) was added. The reaction mixture was stirred for 30 min at the same temperature followed by addition of sodium azide (64 mg, 0.99 mmol). The reaction mixture was stirred at 0° C. for 30 min. When the reaction was complete as confirmed by TLC, reaction mixture was quenched by dropwise addition of 10 N NaOH (5.0 mL). The crude compound was extracted with ethylacetate (2×10 mL). Organic layer was separated, washed with brine, dried over Na2SO4 and the solvents were removed in vacuo to afford (2-azido-benzyl)-carbamic acid tert-butyl ester (105 mg, 96%) which was used as such without any further purification for the next step.

후처리

  1. customReaction mixture
  2. stirringThe reaction mixture was stirred at 0° C. for 30 min
  3. customas confirmed by TLC, reaction mixture
  4. customwas quenched by dropwise addition of 10 N NaOH (5.0 mL)
  5. extractionThe crude compound was extracted with ethylacetate (2×10 mL)
  6. customOrganic layer was separated
  7. washwashed with brine
  8. dry with materialdried over Na2SO4
  9. customthe solvents were removed in vacuo

출처 및 근거

ORD 기록
ord-00b82a900db645fd83ee4571b0549c41
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08455479B2

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