Hydrochloric Acid → 4-(Benzyloxycarbonylamino)thiochromane-7-carboxylic acid

HRID 585725Notes

Reaction equation

HRID 585725 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([CH:9]([NH:15][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[CH2:10][CH2:11][S:12]2)=[CH:7][CH:6]=1)=[O:4].[OH-].[Na+].Cl>CO.O1CCCC1.O>[CH2:19]([O:18][C:16]([NH:15][CH:9]1[C:8]2[C:13](=[CH:14][C:5]([C:3]([OH:4])=[O:2])=[CH:6][CH:7]=2)[S:12][CH2:11][CH2:10]1)=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 696196104-(Benzyloxycarbonylamino)thiochromane-7-carboxylic acid methyl ester

Product 1

HCID 223373434-(Benzyloxycarbonylamino)thiochromane-7-carboxylic acidYield 89.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 4-(benzyloxycarbonylamino)thiochromane-7-carboxylic acid methyl ester (3.20 g) in methanol (50 ml), tetrahydrofuran (100 ml) and water (50 ml) was added 1N aqueous sodium hydroxide solution (20 ml), and the mixture was stirred at room temperature for 5 hr. Dilute hydrochloric acid was added to the reaction mixture until the pH became 1, and the precipitated crystals were collected by filtration. The crystals were recrystallized from acetone-hexane to give the objective 4-(benzyloxycarbonylamino)thiochromane-7-carboxylic acid (2.74 g) as colorless crystals.

Workup

  1. filtrationthe precipitated crystals were collected by filtration
  2. customThe crystals were recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-171592faf648499e84ced80c3d71675a
Source dataset
uspto-grants-2005_08
Patent number
US06933305B2

Reaction notes

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