Methanol → HCID 69428532, compound

HRID 1006779Notes

Reaction equation

HRID 1006779 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][C@H:11]1[CH:25]=O)=[O:9])([CH3:6])([CH3:5])[CH3:4].CO.C([O-])(O)=[O:30].[Na+].[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>>[C:3]([O:7][C:8]([N:10]1[CH2:14][C@H:13]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[CH2:12][C@H:11]1[CH:25]=[CH:35][C:36]([O:37][CH2:38][CH3:34])=[O:30])=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 5

HCID 887MethanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 86584831HCID 86584831, compound

Product 1

HCID 69428532HCID 69428532, compoundYield 40%

Procedure

A solution of 0.91 g (4.08 mmol) triethyl phosphonoacetate in 10 ml THF was first treated with 0.18 g (4.08 mmol) 55% NaH and after cooling (−78° C.) with 1.2 g (3.4 mmol) (2S,4R)-2-formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester. The reaction was warmed up to room temperature and stirred over night. The solution was cooled (0° C.) and treated with 1 ml MeOH followed by 10 ml saturated aqueous Na/K-tartrate and after 10 min with aqueous 10% NaHCO3 solution. The aqueous phase was filtered, extracted (EtOAc 2×) and the organic phase was dried (Na2SO4), evaporated and purified on silica gel column (Hexane/EtOAc 9:1 to 7:3) to give 0.57 g (40%) of (2S,4R)-2-(2-ethoxycarbonyl-vinyl)-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 422 (MH+).

Workup

  1. temperatureThe solution was cooled (0° C.)
  2. filtrationThe aqueous phase was filtered
  3. extractionextracted (EtOAc 2×)
  4. dry with materialthe organic phase was dried (Na2SO4)
  5. customevaporated
  6. custompurified on silica gel column (Hexane/EtOAc 9:1 to 7:3)

Sources & evidence

ORD record
ord-073da4d3114f4cb2b8ceb78d96b9bf2f
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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