(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acid → HCID 19038612, 화합물

HRID 263671

반응식

HRID 263671 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][CH:13]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH:14]([N:16]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:17]([CH:19]1[CH:23]([C:24]([O:26]C(C)(C)C)=[O:25])[CH2:22][C:21](=[O:31])[O:20]1)=[O:18])[CH3:15].C(OC(C1CC(=O)OC1C(O)=O)=O)(C)(C)C.C(C([O-])=O)(C([O-])=O)(C([O-])=O)CC>C(O)=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1/[CH:10]=[CH:11]/[CH2:12][CH:13]([C:43]1[CH:48]=[CH:47][C:46]2[O:49][CH2:50][O:51][C:45]=2[CH:44]=1)[CH:14]([N:16]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1)[C:17]([CH:19]1[CH:23]([C:24]([OH:26])=[O:25])[CH2:22][C:21](=[O:31])[O:20]1)=[O:18])[CH3:15]

참가 물질

5

반응물 3

HCID 18705233(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acidHCID 21864432HCID 21864432, 화합물HCID 86751027HCID 86751027, 화합물

생성물 1

HCID 19038612HCID 19038612, 화합물수율 46.3%

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

47 mg of tert-butyl (2RS,3RS)-2-[N-{(1RS,2RS,4E)-5-(2-benzoxazolyl)-1-methyl-2-(3,4-methylenedioxyphenyl)-4-pentenyl}-N-(2-naphthylmethyl)carbamoyl]-5-oxotetrahydrofuran-3-carboxylate prepared in a manner similar to Example 27 except that (2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acid obtained in Reference Example 4 was used, instead of the 1,2-di-tert-butyl (R*)-1,2,3,-propanetricarboxylate in Example 27, was dissolved in 1 ml of formic acid, and the solution was left to stand at room temperature overnight. The reaction solution was distilled under reduced pressure. Then, toluene was added to the residue, followed by distillation again. The product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)→chloroform/methanol=50/1) to obtain 20 mg (yield: 46%) of the above-identified compound as white solid.

후처리

  1. customobtained in Reference Example 4
  2. waitthe solution was left
  3. distillationThe reaction solution was distilled under reduced pressure
  4. additionThen, toluene was added to the residue
  5. distillationfollowed by distillation again
  6. customThe product was purified by silica gel column chromatography (hexane/ethyl acetate=2/1)→chloroform/methanol=50/1)

출처 및 근거

ORD 기록
ord-c4894186daa94f939824a44874eca284
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643958

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