P,P-Diphenylphosphinic azide → Nalpha-Benzyloxycarbonyl-D-asparaginyl-L-leucine methyl ester

HRID 2083834Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([C:17]([OH:19])=O)[CH2:13][C:14](=[O:16])[NH2:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:21][O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH2:25].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>CN(C)C=O.C(N(CC)CC)C>[CH3:21][O:22][C:23](=[O:30])[C@H:24]([CH2:26][CH:27]([CH3:29])[CH3:28])[NH:25][C:17](=[O:19])[C@@H:12]([CH2:13][C:14](=[O:16])[NH2:15])[NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10]

Participants

Conditions

Temperature: 5 °C

Procedure

Nα -Benzyloxycarbonyl-D-asparagine, 5.325 g., and 3.814 g. of leucine methyl ester hydrochloride are dissolved in 50 ml. of dimethylformamide. The solution is cooled to 5° C. and treated slowly with 3.0 ml. of diphenylphosphorylazide in 10 ml. of dimethylformamide and 5.9 ml. of triethylamine in 10 ml. of dimethylformamide. The reaction is stirred with ice cooling for two and a half hours and at room temperature for three days. The mixture is filtered and the filtrate evaporated to dryness under reduced pressure. The residue is crystallized from ethyl acetate; 2.5 g.; m.p. 191°-193° C.; [α]D25 -14.4° (c 1.015, DMF). A further quantity of material, 1.25 g., is obtainable from the mother liquor of the crystallization.

Workup

additiontreated slowly with 3.0 ml
filtrationThe mixture is filtered
customthe filtrate evaporated to dryness under reduced pressure
customThe residue is crystallized from ethyl acetate
custom, is obtainable from the mother liquor of the crystallization

Sources & evidence

ORD record: ord-656834cb53f044499b4369c37e3f619e
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04086219

Reaction notes

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