Triphenylphosphine → Carbamic acid, [2-oxo-1-(phenylmethoxy)-1-azaspiro[3.3]hept-3-yl]-, 1,1-dimethylethyl ester

HRID 2118841Notes

Reaction equation

[CH2:1]([O:8][NH:9][C:10](=[O:25])[CH:11]([C:20]1(O)[CH2:23][CH2:22][CH2:21]1)[NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>O1CCCC1>[CH2:1]([O:8][N:9]1[C:20]2([CH2:23][CH2:22][CH2:21]2)[CH:11]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:10]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

N-(Benzyloxy)-N2 -(t-butoxycarbonyl)-α-(1-hydroxycyclobutyl)glycinamide (3.50 g, 10 mmole) in 200 ml of dry tetrahydrofuran at 0° C. under argon was treated with 2.4 ml (15 mmole) of diethylazodicarboxylate, then with a solution of triphenylphosphine (5.2 g, 20 mmole) in 50 ml of tetrahydrofuran over 10 minutes, and the mixture stirred at 0° C. for one hour. The yellow color persisted so an additional 0.52 g (2 mmole) of triphenylphosphine was added. After 15 minutes, evaporation in vacuo gave an oil. Trituration with 100 ml of hexane:ethyl acetate (2:1) gave a white solid which was filtered. Chromatography of the filtrate on 800 ml of LPS-1 gave product fractions [Rf=0.8 in hexane:ethyl acetate (1:1)] contaminated with a close-running impurity which was removed by trituration with isopropyl ether, giving the product as a white solid, 1.07 g, melting point 156°-157° C.

Workup

additionwas added
waitAfter 15 minutes
customevaporation in vacuo
customgave an oil
filtrationwas filtered
customwas removed by trituration with isopropyl ether

Sources & evidence

ORD record: ord-fa93a08ebded41e3b77096763eb4101d
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04680388

Reaction notes

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