Hydrochloric Acid → HCID 53634770, compound

HRID 429731Notes

Reaction equation

HRID 429731 reaction equation
C[O:2][C:3](=O)[CH:4]([N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH3:19])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[BH4-].[Li+].CO.Cl>CCOCC>[C:23]([O:22][C:20](=[O:21])[N:18]([CH:4]([CH2:3][OH:2])[CH:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)[CH3:19])([CH3:24])([CH3:26])[CH3:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4148881Lithium borohydrideHCID 53902813HCID 53902813, compound

Product 1

HCID 53634770HCID 53634770, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 32.0 g (86.6 mmol) of 2-(N-tert-butoxycarbonyl-N-methyl-amino)-3,3-diphenyl-propanoic acid methyl ester in 400 ml of ether there are added in succession 3.0 g (130.0 mmol) of lithium borohydride in portions and 5.3 ml (130 mmol) of methanol dropwise (foams!). The reaction mixture is stirred under reflux for 3 hours, then cooled in an ice bath, and 40 ml of 0.5N hydrochloric acid are added (foams!). After further dilution with water, the mixture is extracted twice with methylene chloride. The combined organic phases are dried over sodium sulfate and concentrated by evaporation, yielding the title compound in the form of a white foam. TLC: methylene chloride/methanol (95:5) Rf=0.46; FAB-MS (M+H)+=342.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperaturecooled in an ice bath
  3. extractionAfter further dilution with water, the mixture is extracted twice with methylene chloride
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0062df484e1f49f6be850e89023d81c3
Source dataset
uspto-grants-2001_11
Patent number
US06319917B1

Reaction notes

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