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

HRID 263671

反応式

HRID 263671 の反応式
[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]

参加物

5

反応物 3

HCID 18705233(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acidHCID 21864432HCID 21864432、化合物HCID 86751027HCID 86751027、化合物

生成物 1

HCID 19038612HCID 19038612、化合物収率 46.3%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c4894186daa94f939824a44874eca284
出典データセット
uspto-grants-1997_07
特許番号
US05643958

関連ノート

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