Diethyl Ether → HCID 14181424, compound

HRID 1252804Notes

Reaction equation

HRID 1252804 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([CH:15]=[CH2:16])(=[O:14])=[O:13])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[S:25]1C=CC=C1CC(O)=O.[CH3:34][CH2:35][O:36]CC>>[C:1]([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([CH:15]=[CH2:16])(=[O:13])=[O:14])([CH3:4])([CH3:2])[CH3:3].[C:1]([O:5][C:6](=[O:17])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[S:12]([CH2:15][CH2:16][S:25][C:35](=[O:36])[CH3:34])(=[O:13])=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 159702-Thiopheneacetic acidHCID 14181424HCID 14181424, compound

Product 2

HCID 14181424HCID 14181424, compoundHCID 14181426HCID 14181426, compound

Procedure

N-(Vinylsulfonyl)-L-proline t-butyl ester (5.0 g, 0.0192 mole), triethylamine (2.8 ml, 0.02 mole) and thiolacetic acid (1.43 ml, 0.02 mole) are mixed in 100 ml of ether and allowed to stand overnight. The mixture is washed with 5% potassium bisulfate solution, saturated sodium bicarbonate solution and brine, then evaporated in vacuo to a yellow oil. The procedure is repeated using half of the above quantities of triethylamine and thiolacetic acid. Workup as in part (a) affords the crude product, N-[[2-(acetylthio)ethyl]sulfonyl]-L-proline t-butyl ester, which is filtered through a short silical gel column and crystallized from ether/hexane, m.p. 46°-50° (2.9 g, 45%).

Workup

  1. washThe mixture is washed with 5% potassium bisulfate solution, saturated sodium bicarbonate solution and brine
  2. customevaporated in vacuo to a yellow oil

Sources & evidence

ORD record
ord-44fd48422ddb410d8b31a29b5c1ee5d8
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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