Benzyl chloroformate → 1-Benzyloxycarbonylamino-2-phenylethylphosphonous acid

HRID 1376426Notes

Reaction equation

Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][CH:13]([P:21]([OH:23])[OH:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>[OH-].[Na+].O.O1CCOCC1>[CH2:5]([O:4][C:2]([NH:12][CH:13]([P:21]([OH:23])[OH:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2.25 ml (14.25 mmol) of benzyl chloroformate are added dropwise, at 0° C. and within the space of 30 min., to a suspension of 1.76 g (9.5 mmol) of 1-amino-2-phenylethylphosponous acid in 15 ml of 1M NaOH, 5 ml of water and 5 ml of dioxane. During a further 2.5 h of stirring at 0° C., the pH of the mixture is maintained at 9-10 using 1M NaOH (approximately 10 ml). After removing the cooling medium, the mixture is stirred at RT overnight. The reaction solution is then washed several times with diethyl ether. The aqueous phase is adjusted to pH 2, at 0°-5° C., using 6M HCl and extracted several times with ethyl acetate. The combined extracts are washed with a saturated solution of NaCl, dried with Na2SO4, filtered and subjected to rotary evaporation i.V. A solid residue remains which is recrystallized from ether/petroleum ether.

Workup

customAfter removing the cooling medium
stirringthe mixture is stirred at RT overnight
washThe reaction solution is then washed several times with diethyl ether
customis adjusted to pH 2, at 0°-5° C.
extractionextracted several times with ethyl acetate
washThe combined extracts are washed with a saturated solution of NaCl
dry with materialdried with Na2SO4
filtrationfiltered
customis recrystallized from ether/petroleum ether

Sources & evidence

ORD record: ord-d2956f2c407c4e0ab5daa437bf3e87f1
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663139

Reaction notes

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