Triethylamine → N-(tert-Butoxycarbonyl)-4-nitro-L-phenylalanine

HRID 621764Notes

Reaction equation

[N+:1]([C:4]1[CH:15]=[CH:14][C:7]([CH2:8][C@@H:9]([C:11]([OH:13])=[O:12])[NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:23][C:24]([O:27][C:28](ON=C(C1C=CC=CC=1)C#N)=[O:29])([CH3:26])[CH3:25].C(OCC)(=O)C>O1CCOCC1.O>[C:28]([NH:10][C@H:9]([C:11]([OH:13])=[O:12])[CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:15][CH:14]=1)([O:27][C:24]([CH3:26])([CH3:25])[CH3:23])=[O:29]

Participants

Conditions

Temperature: 0 °C

Procedure

p-Nitrophenylalanine (7.94 g, 37.8 mmol) was dissolved in 50% aqueous dioxane solution (60 ml) and triethylamine (0.9 ml, 56.7 mmol) added. BOC-ON (10.24 g, 41.6 mmol) (Aldrich Chemical Co.) was added and the solution stirred for two hours. Ethyl acetate (100 ml) and H2O (50 ml) were next added and the contents poured into a separatory funnel. The aqueous layer was retained and extracted twice with ethyl acetate (100 ml). The aqueous layer was cooled to 0° C. and the pH was adjusted to 2.0 with 3N HCl, whereupon a precipitate formed which was collected and dried under vacuum. The filtrate was extracted with ethyl acetate twice (100 ml), dried (MgSO4) and stripped to dryness. The two fractions provided to be identical and were combined (11.0 g, 94.0%). The melting point of the compound was 165° C.

Workup

additionthe contents poured into a separatory funnel
extractionextracted twice with ethyl acetate (100 ml)
customformed which
customwas collected
customdried under vacuum
extractionThe filtrate was extracted with ethyl acetate twice (100 ml)
dry with materialdried (MgSO4)
customThe two fractions provided
customwas 165° C.

Sources & evidence

ORD record: ord-fe1136e511fb4651838a4b6f38349b2c
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04824986

Reaction notes

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