Ammonia → 2-[(R)-(Carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide

HRID 78949

반응식

HRID 78949 반응식
[C:1]([C@:3]([NH:14][C@H:15]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:16]([NH2:18])=[O:17])([CH3:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)#[N:2].C(Cl)Cl.[OH:28]S(O)(=O)=O.N>CCOC(C)=O>[C:16]([C@H:15]([NH:14][C@@:3]([CH3:13])([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=1)[C:1]([NH2:2])=[O:28])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:17])[NH2:18]

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 1118Sulfuric AcidHCID 6344DichloromethaneHCID 67200502(R)-2-(((S)-2-cyano-1-(4-methoxyphenyl)propan-2-yl) amino)-2-phenylacetamide

생성물 1

HCID 671670122-[(R)-(Carbamoylphenylmethyl)-amino]-3-(4-methoxyphenyl)-2-(S)-methylpropionamide

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매2회

반응 조건

온도
-10 °C

실험 절차

To a 500 mL flask were added nitrile 2 (10.0 g, 30.95 mmol) and CH2Cl2 (130 mL). The solution was cooled to −10° C. and H2SO4 (10 mL) was added dropwise over 15 min. The mixture was stirred for 2 h at 0° C. Ice (200 g) was added and the mixture was stirred for 1 h. The mixture was basified with 32% aq NH3 to pH 8-9, EtOAc (400 mL) was added and the phases were separated. The aqueous phase was extracted with EtOAc (2×250 mL). The combined organic phases were dried over MgSO4 and were concentrated to provide 3 (11.1 g (9.99 g theoretical, the sample contains 10% w/w of EtOAc by NMR) 94%, 92.9% chemical purity, 97% de by HPLC/MS) as a white solid. HPLC/MS tR=3.04 min; m/z=342.1 (M+1)

후처리

  1. stirringthe mixture was stirred for 1 h
  2. additionwas added
  3. customthe phases were separated
  4. extractionThe aqueous phase was extracted with EtOAc (2×250 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. concentrationwere concentrated
  7. customto provide 3 (11.1 g (9.99 g theoretical

출처 및 근거

ORD 기록
ord-5b7042aa79594fc7986d5d8042e1dca5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841486B2

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