Tert-Butylamine → HCID 70051621, 화합물

HRID 1780273

반응식

HRID 1780273 반응식
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([NH2:22])([CH3:21])([CH3:20])[CH3:19].C(N(CC)CC)C.[CH2:30]([O:37][C:38]([N:40]1[CH2:47][C@@H:46]([OH:48])[CH2:45][C@H:41]1[C:42](O)=[O:43])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CN(C)C=O>[CH2:30]([O:37][C:38]([N:40]1[CH2:47][C@@H:46]([OH:48])[CH2:45][C@H:41]1[C:42]([NH:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:43])=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

참가 물질

6

반응물 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 688414(2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

생성물 1

HCID 70051621HCID 70051621, 화합물수율 24.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4.56 g (16.58 mmol) of diphenylphosphoryl azide, 1.50 g (20.55 mmol) of t-butylamine and 2.78 g (27.80 mmol) of triethylamine were successively added, whilst ice-cooling, to a solution of 3.68 g (13.90 mmol) of (4S)-1-benzyloxycarbonyl-4-hydroxy-L-proline in 30 ml of dimethylformamide, and the mixture was stirred for 5 hours. At the end of this time, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic extract was washed with a 10% w/v aqueous solution of citric acid, with a 10% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which the resulting mixture was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, and the residue was recrystallized from a mixture of methylene chloride and diethyl ether, to give 1.10 g of the title compound as colorless crystals, melting at 129°-130° C.

후처리

  1. extractionextracted with ethyl acetate
  2. extractionThe organic extract
  3. washwas washed with a 10% w/v aqueous solution of citric acid, with a 10% w/v aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  4. dry with materialafter which the resulting mixture was dried over anhydrous sodium sulfate
  5. customThe solvent was then removed by distillation under reduced pressure
  6. customthe residue was recrystallized from a mixture of methylene chloride and diethyl ether

출처 및 근거

ORD 기록
ord-990d51f506bc475787cc715f1ac2efc1
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05629406

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