Hydrochloric Acid → HCID 68718687, compound

HRID 2246706Notes

Reaction equation

HRID 2246706 reaction equation
[C:1]1([O:7][P:8]([CH2:17][C@H:18]([OH:28])[CH2:19][NH:20]C(OC(C)(C)C)=O)([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[ClH:29]>C(OCC)(=O)C>[ClH:29].[C:1]1([O:7][P:8]([CH2:17][C@H:18]([OH:28])[CH2:19][NH2:20])([CH2:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68718986HCID 68718986, compound

Product 1

HCID 68718687HCID 68718687, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. solution of ((R)-3-tert-butoxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid phenyl ester (495 mg, 1.2 mmol) in ethyl acetate (10 mL) was bubbled in HCl gas until saturated, via a pipette at a rate such that the temperature did not exceed 10° C. Once saturated, the reaction mixture was stirred at room temperature for 2 h and then concentrated in vacuo. The resulting residue was triturated with ether (100 mL) and the resulting solid collected to give ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid phenyl ester hydrochloride (248 mg, 0.71 mmol). 1H-NMR (CD3OD, 300 MHz): δ 7.35 (m, 2H), 7.18 (m, 3H), 4.18 (br s, H), 3.21-3.09 (m, 2H), 2.01-1.58 (m, 10H), 1.43-0.95 (m, 9H). 31P NMR (CD3OD, 300 MHz): 57.12, 57.47. LC/MS m/z: [M+H]+=312.

Workup

  1. customdid not exceed 10° C
  2. concentrationconcentrated in vacuo
  3. customThe resulting residue was triturated with ether (100 mL)
  4. customthe resulting solid collected

Sources & evidence

ORD record
ord-215c430604504a4396f6a53d93ee6ef2
Source dataset
uspto-grants-2010_03
Patent number
US07687540B2

Reaction notes

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