Hydrochloric Acid → HCID 69586001, compound

HRID 1745411Notes

Reaction equation

HRID 1745411 reaction equation
C([O:3][C:4]([CH:6]1[O:11][CH2:10][C:9]2[S:12][C:13]([NH2:22])=[C:14]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:8]=2[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl>C(O)C.O1CCCC1>[C:18]([O:17][C:15]([C:14]1[C:8]2[CH2:7][CH:6]([C:4]([OH:5])=[O:3])[O:11][CH2:10][C:9]=2[S:12][C:13]=1[NH2:22])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69586059HCID 69586059, compound

Product 1

HCID 69586001HCID 69586001, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The above 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester 5-ethyl ester (275 mg, 0.84 mmol) was dissolved in a mixture of ethanol (4 ml) and tetrahydrofuran (1 ml). Sodium hydroxide (1N, 1.6 ml, 1.68 mmol) was added and the reaction stirred at ambient temperature for 5 hours after which TLC analysis indicated that the reaction was complete. The reaction was monitored with a pH meter and neutralized with 1N hydrochloric acid until pH=6.9. The solution was concentrated in vacuo to give 2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3,5-dicarboxylic acid 3-tert-butyl ester as a solid. Sodium chloride remained as an impurity.

Workup

  1. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-a1d348965fc74302b04f7a60b8768a9a
Source dataset
uspto-grants-2006_03
Patent number
US07019026B1

Reaction notes

Loading…