Ammonium Chloride → HCID 66988305, compound

HRID 540423Notes

Reaction equation

HRID 540423 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][CH:11]([C:17]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1)=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[Cl-].[NH4+]>C(O)C>[C:3]([O:7][C:8]([NH:10][CH:11]([CH:17]([OH:18])[C:19]1[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 15311957HCID 15311957, compound

Product 1

HCID 66988305HCID 66988305, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
-78 °C

Procedure

461 mg (0.7 mmol) of sodium borohydride are carefully added to a solution of 4.1 mg (12.2 mmol) of ethyl 2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-3-oxo-propanoate in 40 ml of ethanol cooled to −78° C. After stirring for 15 minutes, the reaction medium is hydrolysed with a saturated aqueous solution of ammonium chloride. The ethanol is evaporated off and the aqueous phase is extracted with dichloromethane. The organic phase is dried over magnesium sulphate, filtered and concentrated. The residue is purified by silica gel chromatography, elution being carried out with a 70/30 heptane/ethyl acetate mixture. 3 g of ethyl 2-tert-butoxycarbonylamino-3-hydroxy-3-(4-methoxyphenyl)propanoate are obtained in the form of a yellow oil with a yield of 72%.

Workup

  1. customThe ethanol is evaporated off
  2. extractionthe aqueous phase is extracted with dichloromethane
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-204055ab7dca42c7892ff48921e15a97
Source dataset
uspto-grants-2014_10
Patent number
US08871187B2

Reaction notes

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