HCID 54406880, 화합물 → HCID 53706962, 화합물

HRID 617759노트

반응식

HRID 617759 반응식
[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]

참가 물질

4

반응물 1

HCID 54406880HCID 54406880, 화합물

생성물 1

HCID 53706962HCID 53706962, 화합물수율 100.5%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-84e671bd24194946947c468ed157720c
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05952321

반응 노트

불러오는 중…