Hydrochloric Acid → (2R)-2-{benzyl[methyl(phenyl)phosphoryl]amino}-N-hydroxypropanamide

HRID 355445Notes

Reaction equation

HRID 355445 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH2:22]C(C)C)[N:5]([P@@:13]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:27][O:28][K].Cl>>[OH:28][NH:27][C:3](=[O:2])[C@H:4]([N:5]([P@@:13]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 54435063N-((R)-methylphenylphosphinyl)-N-benzyl-D-leucine methyl esterHCID 178514655HCID 178514655, compound

Product 1

HCID 10664302(2R)-2-{benzyl[methyl(phenyl)phosphoryl]amino}-N-hydroxypropanamide

Procedure

N-((R)-Methylphenylphosphinyl)-N-benzyl-D-leucine methyl ester (181 mg, 0.55 mmol) is treated with a solution of NH2OK (2.2 mL, 1.76M in methanol) prepared as described in Fieser and Fieser, Vol. 1, p. 478). The reaction is stirred for 16 hours at which time TLC indicates completion. The reaction mixture is neutralized with 1M aqueous HCl and the volatiles are removed. The desired product is purified over flash silica eluting with THF. The resulting residue is crystallized by dissolving in ethyl acetate and adding hexane until the solution becomes cloudy. N-Hydroxy-2(R)-[[(R)-methylphenylphosphinyl]-benzylamino]-propionamide is obtained as hard, dense colorless crystals: MS-IS m/z 333 [M+H]+, 355 [M+Na]+. (R1 =benzyl, R2 =methyl, R3 =phenyl, R4 =phenyl).

Workup

  1. customprepared
  2. customthe volatiles are removed
  3. customThe desired product is purified over flash silica eluting with THF
  4. customThe resulting residue is crystallized
  5. dissolutionby dissolving in ethyl acetate
  6. additionadding hexane until the solution

Sources & evidence

ORD record
ord-1c0b92326b654d94815bc5cb7508917a
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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