Hydrochloric Acid → HCID 59864485, compound

HRID 906653Notes

Reaction equation

HRID 906653 reaction equation
[NH:1]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:2]([C:5]([OH:7])=O)[CH2:3][OH:4].[C:18]1([Mg]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl.CCCCCC>C1COCC1.C(OCC)(=O)C>[OH:4][CH2:3][C@H:2]([NH:1][C:8](=[O:9])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5](=[O:7])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 100310N-(Benzyloxycarbonyl)-L-serineHCID 178418255HCID 178418255, compound

Product 1

HCID 59864485HCID 59864485, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of Z-L-Ser-OH (6.00 g, 25.08 mmol) in 32 mL of anhydrous THF at 0° C. under nitrogen was added dropwise 1 M phenylmagnesium bromide in THF (32 mL, 200 mmol). (The symbol Z designates a benzylcarbamoyl group). The mixture was stirred 15 h at RT under nitrogen. A solution of 2 M HCl (100 mL) was slowly added at 0° C. and the mixture was partitioned between ethyl acetate (750 mL) and acidic water. The organic layer was washed with water (2×20 mL), 1 N aqueous sodium bicarbonate (2×20 mL), brine (2×20 mL) and dried over MgSO4. After removing ethyl acetate by evaporation at 30-35° C., the crude product (4.50 g, 60% yield) was crystallized in a mixture of ethyl acetate:hexane=25 mL:20 mL to give benzyl (S)-3-hydroxy-1-oxo-1-phenylpropan-2-ylcarbamate TTA 08010B as a white solid (1.40 g, 20% yield).

Workup

  1. customthe mixture was partitioned between ethyl acetate (750 mL) and acidic water
  2. washThe organic layer was washed with water (2×20 mL), 1 N aqueous sodium bicarbonate (2×20 mL), brine (2×20 mL)
  3. dry with materialdried over MgSO4
  4. customAfter removing ethyl acetate
  5. customby evaporation at 30-35° C.

Sources & evidence

ORD record
ord-f81515208a0b4ee790780ef51731771a
Source dataset
uspto-grants-2011_09
Patent number
US08013000B2

Reaction notes

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