Ethanolamine → HCID 13293005, compound

HRID 464013Notes

Reaction equation

HRID 464013 reaction equation
Br[CH:2]1[CH2:19][C@@:18]([C:21](=[O:27])[CH2:22][O:23][C:24](=[O:26])[CH3:25])([OH:20])[CH2:17][C:16]2[C:15]([OH:28])=[C:14]3[C:5]([C:6](=[O:30])[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]3=[O:29])=[C:4]([OH:31])[C:3]1=2.[CH2:32]([CH2:34][NH2:35])[OH:33]>>[OH:33][CH2:32][CH2:34][NH:35][C@H:2]1[CH2:19][C@@:18]([C:21](=[O:27])[CH2:22][O:23][C:24](=[O:26])[CH3:25])([OH:20])[CH2:17][C:16]2[C:15]([OH:28])=[C:14]3[C:5]([C:6](=[O:30])[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[C:13]3=[O:29])=[C:4]([OH:31])[C:3]1=2

Participants

3

Reactant 2

HCID 700EthanolamineHCID 13146271HCID 13146271, compound

Product 1

HCID 13293005HCID 13293005, compound

Procedure

In the same manner as in Example 4-(1), 7-bromo-9(S)-acetoxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione (200 mg) obtained in Reference Example 4 was treated with ethanolamine (30 mg) and the reaction product was post-treated to give dark reddish brown crystals of 7(S)-β-hydroxyethylamino-9(S)-acetoxyacetyl-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydronaphthacene-5,12-dione. M.P., 100°-103° C. [α]D20 =+166.2° (c=0.1, CHCl3).

Workup

  1. additionthe reaction product was post-treated

Sources & evidence

ORD record
ord-827028ef85fc47d3b3d4b451a546005f
Source dataset
uspto-grants-1985_10
Patent number
US04545936

Reaction notes

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