(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

反応式

HRID 58833 の反応式
[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

参加物

5

反応物 2

HCID 10495486(S)-2-(Boc-amino)-3-cyclohexyl-N-methoxy-N-methylpropanamideHCID 178456138HCID 178456138、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 178479889HCID 178479889、化合物溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-e88b25263caa438cba76295ea3f610bc
出典データセット
uspto-grants-2016_09
特許番号
US09434761B2

関連ノート

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