HCID 54406880、化合物 → HCID 53706962、化合物

HRID 617759ノート

反応式

HRID 617759 の反応式
[C:1]([N:11]([C@@H:13]([CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[CH3:12])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(O)C.Cl>[C:1]([N:11]([C@@H:13]([CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH3:12])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

参加物

4

反応物 1

HCID 54406880HCID 54406880、化合物

生成物 1

HCID 53706962HCID 53706962、化合物収率 100.5%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

α-A solution of (S)-(-)-N-carbobenzyloxy-N-methyl-methyl-4-nitrobenzylamine (6.6 gm, 21 imol) in 100% ethanol (100 mL) was cooled in an ice bath while a solution of stannous chloride dihydrate (14.2 gm, 63 mmol) in conc. hydrochloric acid (25 mL) was added. The reaction was allowed to warm to rt over 14 hrs and was then quenched into a solution of ice, 5N sodium hydroxide (100 mL) and ether and the pH adjusted to 9-10. The layers were separated and the ether layer was washed with brine. The aqueous layers were consecutively extracted with a second portion of ether and the pooled ether layers were dried over sodium sulfate and evaporated. The residue was partially purified by flash chromatography using 20-30% ethyl acetate/hexanes, then 5% methanol/30% ethyl acetate/65% hexanes to give 6.0 gm of impure title compound containing variable amounts of benzyloxycarbonylmethylamine.

後処理

  1. additionwas added
  2. customwas then quenched into a solution of ice, 5N sodium hydroxide (100 mL) and ether
  3. customThe layers were separated
  4. washthe ether layer was washed with brine
  5. extractionThe aqueous layers were consecutively extracted with a second portion of ether
  6. dry with materialthe pooled ether layers were dried over sodium sulfate
  7. customevaporated
  8. customThe residue was partially purified by flash chromatography

出典と根拠

ORDレコード
ord-84e671bd24194946947c468ed157720c
出典データセット
uspto-grants-1999_09
特許番号
US05952321

反応ノート

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