Pyridine → HCID 86585074, compound

HRID 1264423Notes

Reaction equation

HRID 1264423 reaction equation
[CH3:1][O:2][N:3]([CH3:31])[C:4]([C@@H:6]1[CH2:10][C@@H:9]([S:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8][NH:7]1)=[O:5].N1C=CC=CC=1.[CH2:38]([O:42][C:43](Cl)=[O:44])[CH2:39][CH2:40][CH3:41]>C1COCC1>[CH2:38]([O:42][C:43]([N:7]1[CH2:8][C@H:9]([S:11][C:12]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:10][C@H:6]1[C:4](=[O:5])[N:3]([O:2][CH3:1])[CH3:31])=[O:44])[CH2:39][CH2:40][CH3:41]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61140Butyl chloroformateHCID 86585075HCID 86585075, compound

Product 1

HCID 86585074HCID 86585074, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 17.3 g (40 mmol) (2S,4R)-4-Tritylsulfanyl-pyrrolidine-2-carboxylic acid methoxy-methyl-amide in 120 ml THF was treated at 0° C. with 4 ml (50 mmol) pyridine and 5.59 ml (42 mmol) butylchloroformate. The reaction was warmed up to RT over night, evaporated and partitioned between aqueous 10% KHSO4/Et2O (3×). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl and dried over Na2SO4. Purification by flash-chromatography on silicagel (Hexane/EtOAc 4:1) gave 20.4 g (96%) of (2S,4R)-2-(Methoxy-methyl-carbamoyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid butyl ester, MS: 533 (MH+).

Workup

  1. customevaporated
  2. custompartitioned between aqueous 10% KHSO4/Et2O (3×)
  3. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  4. dry with materialdried over Na2SO4
  5. customPurification by flash-chromatography on silicagel (Hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-3983888f36fc45cf9c2f9551aa382c47
Source dataset
uspto-grants-2003_04
Patent number
US06541638B2

Reaction notes

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