(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamide → (S)-tert-butyl (1-cyclohexyl-4-methyl-3-oxopent-4-en-2-yl)carbamate

HRID 58833

반응식

HRID 58833 반응식
[CH:1]1([CH2:7][C@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[C:9](N(OC)C)=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:23]([Mg]Br)([CH3:25])=[CH2:24]>C1COCC1.CN1C2C(N=C(N)NC=2NCC1CNC1C=CC(C(NC(C(O)=O)CCC(O)=O)=O)=CC=1)=O>[CH:1]1([CH2:7][C@H:8]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[C:9](=[O:10])[C:23]([CH3:25])=[CH2:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

5

반응물 2

HCID 10495486(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamideHCID 178456138HCID 178456138, 화합물

생성물 1

HCID 117608154(S)-tert-butyl (1-cyclohexyl-4-methyl-3-oxopent-4-en-2-yl)carbamate수율 49%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 178479889HCID 178479889, 화합물용매

반응 조건

온도
0 °C

실험 절차

To (S)-tert-butyl (3-cyclohexyl-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate (12.2 g, 38.9 mmol) in THF (150 mL) at 0° C. was added isopropenylmagnesium bromide (71.2 mL of a 1.5 N solution in methyl-THF, 0.107 mol) dropwise. After stirring at 0° C. for 2 h the mixture was quenched with heptane/citric acid (1:1). The product was extracted with EtOAc (2×), washed with brine, dried with sodium sulfate, filtered, and concentrated. The crude product was triturated from cold (0° C.) methanol to provide (S)-tert-butyl (1-cyclohexyl-4-methyl-3-oxopent-4-en-2-yl)carbamate (5.36 g, 49%) as a colorless crystalline solid. MS (EI) for C17H29NO3, found 196.2 [M-Boc]+.

후처리

  1. customwas quenched with heptane/citric acid (1:1)
  2. extractionThe product was extracted with EtOAc (2×)
  3. washwashed with brine
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was triturated from cold (0° C.) methanol

출처 및 근거

ORD 기록
ord-e88b25263caa438cba76295ea3f610bc
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434761B2

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