Hydrochloric Acid → 3-Hydroxy-4-[(2-hydroxy-ethylamino)-methyl]-8-methoxy-1,9-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid

HRID 1692627Notes

Reaction equation

HRID 1692627 reaction equation
[CH3:1][C:2]1[C:7]2[C:8]([O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=3[O:17][C:6]=2[C:5]([CH:24]=O)=[C:4]([OH:26])[CH:3]=1)=[O:9].[NH2:27][CH2:28][CH2:29][OH:30].[BH4-].[Na+].Cl>C(O)C.O>[OH:26][C:4]1[CH:3]=[C:2]([CH3:1])[C:7]2[C:8](=[O:9])[O:10][C:11]3[C:12]([CH3:23])=[C:13]([O:21][CH3:22])[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[C:16]=3[O:17][C:6]=2[C:5]=1[CH2:24][NH:27][CH2:28][CH2:29][OH:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 700EthanolamineHCID 23725Psoromic AcidHCID 4311764Sodium borohydride

Product 1

HCID 672801213-Hydroxy-4-[(2-hydroxy-ethylamino)-methyl]-8-methoxy-1,9-dimethyl-11-oxo-11h-dibenzo[b,e][1,4]dioxepine-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirring solution of psoromic acid (1 mmol) in ethanol (25 mL) was added 2-amino-ethanol (1 mmol). The reaction was stirred for half an hour. The reaction was added with sodium borohydride (4 mmol) under ice bath, and stirred for additional 15 min under ice bath and then allowed to react overnight at room temperature. Water (3 mL) was added, the solution was acidified to a pH of 6 with dilute HCl. All of the solvent was removed by rotary evaporation. The residue was redissolved in ethanol and dried over anhydrous magnesium sulfate, filtered, and evaporated by a rotary evaporator to give a white solid product.

Workup

  1. stirringstirred for additional 15 min under ice bath
  2. customto react overnight at room temperature
  3. customAll of the solvent was removed by rotary evaporation
  4. dissolutionThe residue was redissolved in ethanol
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated by a rotary evaporator
  8. customto give a white solid product

Sources & evidence

ORD record
ord-1d410561643e4712a9c6539cfe8880b1
Source dataset
uspto-grants-2012_04
Patent number
US08158623B2

Reaction notes

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