Triethylamine → N-(thiazol-5-ylmethoxycarbonyl)-N,N-bis[(2S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine

HRID 39385

반응식

HRID 39385 반응식
[S:1]1[C:5]([CH2:6][O:7][C:8]([NH:10][C@@H:11]([CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:12][NH:13][CH2:14][C@@H:15]([NH:23][C:24]([O:26][CH2:27][C:28]2[S:32][CH:31]=[N:30][CH:29]=2)=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:9])=[CH:4][N:3]=[CH:2]1.[C:40](=O)([O:51][CH2:52][C:53]1[S:57][CH:56]=[N:55][CH:54]=1)[O:41]C1C=CC([N+]([O-])=O)=CC=1.C(N(CC)CC)C>C(OCC)(=O)C>[S:57]1[C:53]([CH2:52][O:51][C:40]([N:13]([CH2:14][C@@H:15]([NH:23][C:24]([O:26][CH2:27][C:28]2[S:32][CH:31]=[N:30][CH:29]=2)=[O:25])[CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:12][C@@H:11]([NH:10][C:8]([O:7][CH2:6][C:5]2[S:1][CH:2]=[N:3][CH:4]=2)=[O:9])[CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[O:41])=[CH:54][N:55]=[CH:56]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateHCID 11854723N,N-bis[(2S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine

생성물 1

HCID 11856339N-(thiazol-5-ylmethoxycarbonyl)-N,N-bis[(2S)-2-(thiazol-5-ylmethoxycarbonylamino)-3-phenylpropyl]amine수율 36%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

The product from Example 35 (30 mg, 0.053 mmol) in ethyl acetate (2 mL) was treated with a solution of 4-nitrophenyl 1,3-thiazol-5-ylmethyl carbonate [prepared from 4-nitrophenyl 1,3-thiazol-5-ylmethyl carbonate hydrochloride salt (18 mg, 0.058 mmol) by extraction with aqueous NaHCO3], triethylamine (15 μl, 0.106 mmol), and N,N-dimethylaminopyridine (6 mg, 0.053 mmol) at ambient temperature. After stirring for 18 hours, the mixture was washed with aqueous 10% K2CO3 (5×2 mL), brine (2 mL), dried over sodium sulfate, filtered, and the filtrate was concentrated. The residue was purify on a silica gel cartridge eluting with (chloroform:methanol, 99:1) to provide the title compound (13.4 mg, 36%). 1H NMR (CDCl3) δ 8.80-8.68 (m, 3H), 7.81 (m, 3H), 7.31-6.96 (m, 10H), 5.27-5.05 (m, 6H), 4.04-3.25 (m, 5H), 3.11-2.98 (m, 2H), 2.89-2.56 (m, 5H); MS (ESI+) m/z 707 (M+H)+.

후처리

  1. washthe mixture was washed with aqueous 10% K2CO3 (5×2 mL), brine (2 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purify on a silica gel cartridge
  6. washeluting with (chloroform:methanol, 99:1)

출처 및 근거

ORD 기록
ord-67b6c1a9176248c391051f2a56e03dff
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524753B2

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