Ethanol → HCID 131719713, compound

HRID 1900992Notes

Reaction equation

HRID 1900992 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[CH:8]=[CH:9][NH:10]2.[Cl:15][C:16]1[C:24]2[CH:23]=[C:22]([C:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH:30]=3)[S:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.C(O)C.[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36]>C(OCC)(=O)C>[C:34]([OH:39])(=[O:38])[C:35]([OH:37])=[O:36].[Cl:15][C:16]1[C:24]2[CH:23]=[C:22]([C:25]3[CH2:26][CH2:27][N:28]([CH2:3][C@H:2]([OH:1])[CH2:4][O:5][C:6]4[CH:14]=[CH:13][CH:12]=[C:11]5[C:7]=4[CH:8]=[CH:9][NH:10]5)[CH2:29][CH:30]=3)[S:21][C:20]=2[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 971Oxalic AcidHCID 10943254(2s)-Glycidyl indol-4-yl etherHCID 21268220HCID 21268220, compound

Product 1

HCID 131719713HCID 131719713, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in a fashion similar to that described in Example 1 using (S)-(+)-4-(oxiranylmethoxy)-1H-indole (0.129 g, 0.068 mmol) and 4-chloro-2-(1,2,3,6-tetrahydropyridin-4-yl)benzo[b]thiophene (0.170 g, 0.068 mmol) using ethanol as reaction solvent. Yield 0.105 g (34%) of a tan powder. FDMS m/e=438 (M+ of free base). A sample was dissolved in ethyl acetate and treated with 1.0 equivalent of oxalic acid and evaporated to an orange powder. mp 138°-142° C. (dec) α[D]589 =-5.3 (c=1.13, dimethylsufoxide).

Workup

  1. customas reaction solvent
  2. customevaporated to an orange powder

Sources & evidence

ORD record
ord-eedcfaf1585444d0baff5d7cd7edf1d2
Source dataset
uspto-grants-1996_11
Patent number
US05576321

Reaction notes

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