Benzyl chloroformate → HCID 68719246, compound

HRID 2246701Notes

Reaction equation

HRID 2246701 reaction equation
[NH2:1][CH2:2][C@@H:3]([OH:15])[CH2:4][P:5]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:7])[OH:6].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>O.C1COCC1.C(OCC)(=O)C.Cl>[CH2:26]([O:25][C:23]([NH:1][CH2:2][C@@H:3]([OH:15])[CH2:4][P:5]([CH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(=[O:6])[OH:7])=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 5310935[(2R)-3-amino-2-hydroxypropyl]-(cyclohexylmethyl)phosphinic acid

Product 1

HCID 68719246HCID 68719246, compoundYield 93.3%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of ((R)-3-amino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid (7.05 g, 30 mmol) and potassium carbonate (12.42 g, 90 mmol) in water (90 mL) and THF (30 mL) was added benzyl chloroformate (7.65 g, 45 mmol). After stirring for 3 h at room temperature, the reaction mixture was diluted with ethyl acetate (150 mL) and 2N HCl (90 mL). After stirring vigorously for 10 min the aqueous layer was removed and the organic layer was diluted with heptane (200 mL). The resulting white precipitate was collected to yield ((R)-3-benzyloxycarbonylamino-2-hydroxy-propyl)-cyclohexylmethyl-phosphinic acid (10.5 g, 28 mmol). 1H NMR (CDCl3, 300 MHz): δ 7.32 (m, 5H), 5.45 (br s, 1H), 5.10 (s, 2H), 4.2 (m, 1H), 3.4 (dd, 1H), 3.20 (dd, 1H), 2.01-1.55 (m, 10H), 1.40-0.95 (m, 5H). 31P NMR (CDCl3, 300 MHz): δ 57.3. LC/MS m/z: [M+H]+=370.

Workup

  1. stirringAfter stirring vigorously for 10 min the aqueous layer
  2. customwas removed
  3. additionthe organic layer was diluted with heptane (200 mL)
  4. customThe resulting white precipitate was collected

Sources & evidence

ORD record
ord-bbdb7b81cb6b41e896824edb573535bc
Source dataset
uspto-grants-2010_03
Patent number
US07687540B2

Reaction notes

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