Water → HCID 70129292, compound

HRID 1004324Notes

Reaction equation

HRID 1004324 reaction equation
[CH2:1]([O:3][C:4]([C:6](=[C:15]([C:20](=[O:60])[N:21]([CH:33]([CH3:59])[CH:34]([CH2:50][O:51][Si](C(C)(C)C)(C)C)[CH2:35][C:36]1[O:37][C:38]([C:41](=[O:49])[NH:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[CH:39][CH:40]=1)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[O:16][CH2:17][O:18][CH3:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])[CH3:2].C1C2C(=CC=CC=2)C=CC=1CNC(C)C(CO[Si](C(C)(C)C)(C)C)CC1OC(C(=O)NC2C=CC=CC=2)=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH2:1]([O:3][C:4]([C:6](=[C:15]([C:20](=[O:60])[N:21]([CH:33]([CH3:59])[CH:34]([CH2:50][OH:51])[CH2:35][C:36]1[O:37][C:38]([C:41](=[O:49])[NH:42][C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)=[CH:39][CH:40]=1)[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=1)[O:16][CH2:17][O:18][CH3:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 18794892HCID 18794892, compoundHCID 54528403HCID 54528403, compound

Product 1

HCID 70129292HCID 70129292, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

400 mg of tert-butyl 3-(ethoxycarbonyl)-4-[N-[(1RS,2RS)-2-(tert-butyldimethylsilyloxymethyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]-N-(2-naphthylmethyl)carbamoyl]-4-methoxymethyloxy-3-butenoate prepared by the same reaction as in Example 1(2) by using N-(2-naphthylmethyl)-[(1RS,2RS)-2-(tert-butyldimethylsilyloxymethyl)-1-methyl-3-{5-(phenylcarbamoyl)-2-furyl}propyl]amine prepared in Reference Example 4 was dissolved in 4 ml of tetrahydrofuran and stirred together with 0.95 ml of 1.0M tetrabutylammonium fluoride in tetrahydrofuran solution at room temperature for 2 hours. The reaction solution was poured into water and extracted with ethyl acetate, and the organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The desiccant was filtered off, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography [hexane/ethyl acetate=1/1] to give 147 mg (yield: 43%) of the title compound as a colorless oily substance.

Workup

  1. customprepared in Reference Example 4
  2. extractionextracted with ethyl acetate
  3. washthe organic layer was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe desiccant was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by column chromatography [hexane/ethyl acetate=1/1]

Sources & evidence

ORD record
ord-1808d9096ea642ddbb2639880a09f2f9
Source dataset
uspto-grants-2000_04
Patent number
US06048894

Reaction notes

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