Toluene → ((1S)-1-azidomethyl-2-methylpropyl)carbamic acid t-butyl ester

HRID 891764노트

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HRID 891764 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12]O)[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2].C1(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6](=[O:14])[NH:7][C@H:8]([CH2:12][N:29]=[N+:30]=[N-:31])[CH:9]([CH3:11])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

참가 물질

7

반응물 5

HCID 1140TolueneHCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 7021464tert-butyl N-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamate

생성물 1

HCID 10082502((1S)-1-azidomethyl-2-methylpropyl)carbamic acid t-butyl ester수율 96.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ((1S)-1-hydroxymethyl-2-methylpropyl)carbamic acid t-butyl ester (3.00 g, 14.8 mmol) (obtained as described in Reference Example 61(1)) in tetrahydrofuran (150 ml) were added diphenylphosphoryl azide (4.78 ml, 22.2 mmol), triphenylphosphine (5.82 g, 22.2 mmol) and a 40% solution of diethylazodicarboxylate in toluene (9.67 g, 22.2 mmol) in an ice bath under an atmosphere of nitrogen, and the mixture was stirred for 2 hours under the same conditions. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (9:1) as the eluant to afford ((1S)-1-azidomethyl-2-methylpropyl)carbamic acid t-butyl ester (3.26 g, yield 90%) as a colorless oil.

후처리

  1. customthe completion of the reaction
  2. customthe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-5d559e339177483dbb46723fa7ae3158
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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