Ethanol → HCID 53667775, compound

HRID 903461Notes

Reaction equation

HRID 903461 reaction equation
[H-].[Na+].[S:3]1C=CC=C1CC(O)=O.Br[CH:13]([C:25]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)=[O:26])[CH2:14][C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16].[CH2:37]([OH:39])[CH3:38]>>[C:37]([S:3][CH:13]([C:25]([C:27]1[CH:36]=[CH:35][C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=1)=[O:26])[CH2:14][C:15]([N:17]1[CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([OH:21])=[O:20])=[O:16])(=[O:39])[CH3:38]

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 159702-Thiopheneacetic acidHCID 24758Sodium hydrideHCID 54462396HCID 54462396, compound

Product 1

HCID 53667775HCID 53667775, compound

Procedure

To 30 ml. of ethanol cooled in an ice bath is added 380 mg. of sodium hydride (60% dispersion in oil), and 0.67 ml. of thiolacetic acid. After stirring for 30 minutes, 2.55 g. of 1-[3-bromo-3-(2-naphthoyl)propionyl]-L-proline is added and the mixture is stirred for 18 hours. The solvent is removed under vacuum. The residue is chromatographed on a silica gel column with ethyl acetate-hexane-acetic acid (7.5:2.5:0.2) as solvent to give 1.2 g. of the product of the example, as a white glass, [α]D -36(c, 0.96 ethanol).

Workup

  1. additionis added 380 mg
  2. stirringthe mixture is stirred for 18 hours
  3. customThe solvent is removed under vacuum
  4. customThe residue is chromatographed on a silica gel column with ethyl acetate-hexane-acetic acid (7.5:2.5:0.2) as solvent
  5. customto give 1.2 g

Sources & evidence

ORD record
ord-d82cf73917d8412488336f5bcd3aafa4
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

Loading…