(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acid → (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-carboxylic Acid

HRID 263671

Reaction equation

HRID 263671 reaction equation
[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]

Participants

5

Reactant 3

HCID 18705233(2RS,3RS)-3-tert-butoxycarbonyl-5-oxotetrahydrofuran-2-carboxylic acidHCID 218644321,1,1-PropanetricarboxylateHCID 86751027tert-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

Product 1

HCID 19038612(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-carboxylic AcidYield 46.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-c4894186daa94f939824a44874eca284
Source dataset
uspto-grants-1997_07
Patent number
US05643958

Linked notes

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