4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate → n-(2,2-Dimethylpropyl)-n,n-bis[(2r)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine

HRID 39368

반응식

HRID 39368 반응식
[NH2:1][CH:2]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:3][N:4]([CH2:10][CH:11]([NH2:19])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5][C:6]([CH3:9])([CH3:8])[CH3:7].[C:27](=[O:45])([O:38][CH2:39][C:40]1[S:44][CH:43]=[N:42][CH:41]=1)OC1C=CC([N+]([O-])=O)=CC=1>C(OCC)(=O)C>[CH3:7][C:6]([CH3:9])([CH3:8])[CH2:5][N:4]([CH2:3][C@H:2]([NH:1][C:27]([O:38][CH2:39][C:40]1[S:44][CH:43]=[N:42][CH:41]=1)=[O:45])[CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH2:10][C@H:11]([NH:19][C:27]([O:38][CH2:39][C:40]1[S:44][CH:43]=[N:42][CH:41]=1)=[O:45])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

4

반응물 2

HCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateHCID 66639993n,n-Bis[2-amino-3-phenylpropyl]-n-(2,2-dimethylpropyl)amine

생성물 1

HCID 11853692n-(2,2-Dimethylpropyl)-n,n-bis[(2r)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매3회

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온도
60 °C

실험 절차

The product from Example 7C (0.34 g) was treated with 4-nitrophenyl 1,3-thiazol-5-ylmethyl carbonate [prepared from 4-nitrophenyl 1,3-thiazol-5-ylmethyl carbonate hydrochloride salt (0.63 g, 1.99 mmol) by extraction with aqueous NaHCO3] in ethyl acetate (10 mL). The mixture was stirred at 60° C. under a N2 atmosphere overnight. The mixture was diluted with ethyl acetate (50 mL), extracted with 10% aqueous K2CO3 (3×20 mL), washed with water (20 mL) and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (ethyl acetate:hexanes, 2:1) to provide the two title compounds combined and a third separated product. The mixture of (S,S) and (R,R) enantiomers were obtained as a colorless amorphous solid. Rf=0.32 (ethyl acetate); 1H NMR (CDCl3) δ 8.73 (s, 2H), 7.75 (s, 2H), 7.30-7.11 (m, 10H), 5.53 (br s, 2H), 5.23 (d, J=12.9 Hz, 2H), 5.16 (d, J=13.2 Hz, 2H), 3.91 (m, 2H), 2.90-2.79 (m, 2H), 2.68 (dd, J=7.5, 13.6 Hz, 2H), 2.42 (t, J=12 Hz, 2H), 2.26 (dd, J=1, 12 Hz, 2H), 1.99 (d, J=13.9 Hz, 1H), 1.87 (d, J=14.2 Hz, 1H), 0.71 (s, 9H); MS (ESI+) m/z 636 (M+H)+.

후처리

  1. extractionextracted with 10% aqueous K2CO3 (3×20 mL)
  2. washwashed with water (20 mL) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto provide the two title compounds
  7. additionThe mixture of (S,S)
  8. custom(R,R) enantiomers were obtained as a colorless amorphous solid

출처 및 근거

ORD 기록
ord-28ce3f3d84d3461ab02200ce8c8e5a78
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524753B2

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