Di-benzoyl-d-tartaric acid → HCID 131718337, compound

HRID 2210267Notes

Reaction equation

HRID 2210267 reaction equation
[NH2:1][CH:2]1[CH:7]([OH:8])[C:6]([CH3:10])([CH3:9])[O:5][C:4]2[CH:11]=[CH:12][S:13][C:3]1=2.[C:14]([C@:22]([C:37]([OH:39])=[O:38])([OH:36])[C@:23]([C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([OH:27])[C:24]([OH:26])=[O:25])(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:28]([C@:23]([C:24]([OH:26])=[O:25])([OH:27])[C@:22]([C:14](=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([OH:36])[C:37]([OH:39])=[O:38])(=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH2:1][C@H:2]1[C@H:7]([OH:8])[C:6]([CH3:9])([CH3:10])[O:5][C:4]2[CH:11]=[CH:12][S:13][C:3]1=2

Participants

3

Reactant 2

HCID 12362977Di-benzoyl-d-tartaric acidHCID 14986532HCID 14986532, compound

Product 1

HCID 131718337HCID 131718337, compoundYield 43.3%

Procedure

A solution of 7-amino-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran (1.73 g, 9.69 mmol) was treated with dibenzoyl-D-tartaric acid (3.3 g, 8.69 mmol) and stirred at rt f or 30 min. The mixture was concentrated in vacuo and recrystallized from ethanol to yield 2.1 g (43%) of trans-7-amino-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran dibenzoyl-D-tartrate: mp 176°-177° C.; MS: m/z 200(MH+); αD° =+75.8° (MeOH) Anal. Calcd. for C27H27NO10S: C,58.16; H,4.88; N,2.51.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-da5541ce529944ee88d9bf967b48935c
Source dataset
uspto-grants-1995_10
Patent number
US05457212

Reaction notes

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