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N,N-dimethylhydroxylamine hydrochloride → (S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

HRID 990397
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HRID 990397 반응식
[C:1]([O:5][C:6]([N:8]([CH3:17])[C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.Cl.CN(C)O.CN([C:35]([O:39][N:40]1N=NC2C=CC=C[C:41]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O>[C:1]([O:5][C:6](=[O:7])[N:8]([C@H:9]([C:14](=[O:16])[N:40]([O:39][CH3:35])[CH3:41])[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:17])([CH3:2])([CH3:3])[CH3:4]
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참가 물질

7

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HCID 27969N,N-dimethylhydroxylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7010555(2S)-2-{[(tert-butoxy)carbonyl](methyl)amino}-4-methylpentanoic acid

생성물 1

HCID 53718737(S)-[1-(Methoxy-methyl-carbamoyl)-3-methyl-butyl]-methyl-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

N-tert-butoxycarbonyl-N-methyl-L-leucine (5.0 g, 20.4 mmol) was dissolved in DMF (100 mL), treated with treated with N,N-diisopropylethylamine (28 mL, 163 mmol), N,N-dimethylhydroxylamine hydrochloride salt (2.0 g, 20.4 mmol), and HBTU (7.73 g, 20.4 mmol), then stirred overnight at room temperature. The reaction was diluted with EtOAc (500 mL), washed with saturated bicarbonate solution and brine, dried over Na2SO4, and concentrated to give the desired product as an oil; MS: 289.2 (M+1 for C14H28N2O4); TLC (SiO2) Rf 0.39 (8% MeOH/CH2Cl2), visualized with ninhydrin.

후처리

  1. additiontreated
  2. washwashed with saturated bicarbonate solution and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-35fb4a47a94e4e6e8e37ae931acaa064
출처 데이터셋
uspto-grants-2002_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06458781B1

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