Aniline → N-phenyl-2(S)-(tert-butoxycarbonylamino)-3-phenylpropanamine

HRID 342627노트

반응식

HRID 342627 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:8]([O:12][C:13]([NH:15][C@@H:16]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:17]=O)=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:2]1([NH:1][CH2:17][C@@H:16]([NH:15][C:13]([O:12][C:8]([CH3:9])([CH3:11])[CH3:10])=[O:14])[CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 6115AnilineHCID 5049666Sodium triacetoxyborohydrideHCID 6998013tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

생성물 1

HCID 10568153N-phenyl-2(S)-(tert-butoxycarbonylamino)-3-phenylpropanamine

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

Aniline (3.00 mL, 32.9 mmol) was dissolved in dichloroethane under nitrogen. The product from Step B was added (7.0 g, 29.91) and the reaction stirred for 1 h at room temperature. Sodium triacetoxyborohydride (9.51 g, 44.86 mmol) was added, and the pH adjusted to 5. The reaction was stirred overnight, then quenched with saturated sodium bicarbonate solution. The aqueous layer was removed, the organic phase washed with saturated brine and dried over magnesium sulfate. The title compound was obtained after chromatography on silica get with 8% ethyl acetate in hexane.

후처리

  1. stirringThe reaction was stirred overnight
  2. customquenched with saturated sodium bicarbonate solution
  3. customThe aqueous layer was removed
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate

출처 및 근거

ORD 기록
ord-f57ec193bbda4bb2aa202df914e8578b
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05859012

반응 노트

불러오는 중…