Triethylamine → (S)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-oxazolidine-3-carboxylic acid benzyl ester

HRID 737172노트

반응식

HRID 737172 반응식
[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16]([OH:18])=O)[CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.FC(F)(F)C(OC1C(F)=C(F)C(F)=C(F)C=1F)=O.FC(F)(F)C(O)=O.[NH2:51][C:52]1[S:53][CH:54]=[C:55]([C:57]2[CH:68]=[CH:67][C:60]([C:61]([NH:63][CH:64]3[CH2:66][CH2:65]3)=[O:62])=[CH:59][CH:58]=2)[N:56]=1>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[C@H:15]([C:16](=[O:18])[NH:51][C:52]2[S:53][CH:54]=[C:55]([C:57]3[CH:58]=[CH:59][C:60]([C:61](=[O:62])[NH:63][CH:64]4[CH2:66][CH2:65]4)=[CH:67][CH:68]=3)[N:56]=2)[CH2:14][O:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 688328(-)-3-(Benzyloxycarbonyl)-4-oxazolidinecarboxylic acidHCID 4327891Pentafluorophenyl TrifluoroacetateHCID 866164294-(2-Amino-thiazol-4-yl)-n-cyclopropyl-benzamide trifluoroacetic acid salt

생성물 1

HCID 57849690(S)-4-[4-(4-Cyclopropylcarbamoyl-phenyl)-thiazol-2-ylcarbamoyl]-oxazolidine-3-carboxylic acid benzyl ester

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

(S)-Oxazolidine-3,4-dicarboxylic acid 3-benzyl ester (51.3 mg, 0.20 mmol) was dissolved in DMF (1.5 mL). Triethylamine (56 μL, 0.40 mmol) and pentafluorophenyl trifluoroacetate (35 μL, 0.20 mmol) were added, and the reaction was allowed to stir at ambient temperature for 25 minutes. Then 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide trifluoroacetic acid salt (148.8 mg, 0.40 mmol) was added, and the reaction was stirred at ambient temperature overnight. The reaction was filtered and purified by reverse phase HPLC to give the desired product. Yield 10.2 mg. MS: 493.1 (M+H+); H1 NMR (DMSO-d6): δ(ppm) 0.52-0.74 (m, 4H), 4.05-4.37 (m, 2H), 4.58-4.69 (m, 1H), 4.90-5.17 (m, 4H), 7.00-7.45 (m, 4H), 7.72-7.98 (m, 5H), 8.37-8.48 (m, 1H), 12.48-12.51 (s, 1H).

후처리

  1. stirringthe reaction was stirred at ambient temperature overnight
  2. filtrationThe reaction was filtered
  3. custompurified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-0f5490f86f6a4bfca8a7be48ded3d6ce
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07595398B2

반응 노트

불러오는 중…