Ammonium formate → HCID 23003986、化合物

HRID 396728ノート

反応式

HRID 396728 の反応式
[C:1]([NH:8][C@@H:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[N:21]=[CH:20][CH:19]=[CH:18]2)[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])=O.[NH4+]>C(O)C.[Pd]>[C:1]([NH:8][CH:9]([CH2:14][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][CH:24]=1)[NH:21][CH2:20][CH2:19][CH2:18]2)[C:10]([O:12][CH3:13])=[O:11])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

参加物

5

反応物 2

HCID 2723923Ammonium formate2 回HCID 86685771methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(quinolin-6-yl)propanoate

生成物 1

HCID 23003986HCID 23003986、化合物収率 98.8%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒2 回HCID 702Ethanol溶媒

実験手順

A solution of methyl (S) 2-(N-boc-amino)-3-quinolin-6-yl-propionate [3.8 g, Reference Example 20(a)] in ethanol (100 ml) at 60° C. was treated with ammonium formate (10 g) and 10% palladium on charcoal (500 mg). After stirring at 60° C. further ammonium formate (about 5 g) and palladium on charcoal (about 250 mg) were added, and this was repeated at 30 minute intervals for a further 2 hours, at which time TLC analysis indicated the reaction was complete. After cooling to room temperature the mixture was filtered through Celite to remove spent catalyst, and the filtrate was evaporated. The residue was partitioned between ethyl acetate (200 ml) and sodium bicarbonate solution (200 ml). The organic phase was dried and evaporated to give the title compound (3.8 g) as a colourless oil which slowly crystallised on standing.

後処理

  1. additionwere added
  2. waitintervals for a further 2 hours
  3. filtrationwas filtered through Celite
  4. customto remove
  5. customthe filtrate was evaporated
  6. customThe residue was partitioned between ethyl acetate (200 ml) and sodium bicarbonate solution (200 ml)
  7. customThe organic phase was dried
  8. customevaporated

出典と根拠

ORDレコード
ord-ad8bdba56cd04734810cac81032fc0b2
出典データセット
uspto-grants-2003_08
特許番号
US06608084B1

反応ノート

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