Diethyl Ether → HCID 14181426, compound

HRID 2308774Notes

Reaction equation

HRID 2308774 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]([CH2:15][CH2:16][S:25][C:35](=[O:36])[CH3:34])(=[O:13])=[O:14])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

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

Product 1

HCID 14181426HCID 14181426, compound

Procedure

N-(Vinylsulfonyl)-L-proline t-butyl ester (5.0 g., 0.0192 mol.), triethylamine (2.8 ml., 0.02 mol.) and thiolacetic acid (1.43 ml., 0.02 mol.) 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 silica 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-3a4003873f814600a1e0c447833af6d4
Source dataset
uspto-grants-1987_09
Patent number
US04690936

Reaction notes

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