Hydrochloric Acid → HCID 69818058, compound

HRID 2417411Notes

Reaction equation

HRID 2417411 reaction equation
[C:1]([NH:9][C:10]1[CH:30]=[CH:29][C:13]([CH2:14][C@H:15]2[CH2:19][O:18]C(C)(C)[N:16]2C(OC(C)(C)C)=O)=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO.C(OCC)(=O)C>[NH2:16][C@H:15]([CH2:19][OH:18])[CH2:14][C:13]1[CH:12]=[CH:11][C:10]([NH:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86591184HCID 86591184, compound

Product 1

HCID 69818058HCID 69818058, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of tert-butyl (S)-4-[4-(benzoylamino)benzyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (690 mg) in methanol (20 ml) was added 4N hydrogen chloride in ethyl acetate (5 ml) at room temperature, and the solution was stirred at the same temperature for 4 hours. The mixture was evaporated in vacuo, and the residue was partitioned between chloroform and saturated sodium bicarbonate solution. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated to give (S)-N-[4-(2-amino-3-hydroxypropyl)phenyl]benzamide (250 mg) as a colorless solid.

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was partitioned between chloroform and saturated sodium bicarbonate solution
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5759b84df3df486eaa14b9d98bda5b7f
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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