Water → N-[(1,1-Dimethylethoxy)carbonyl]-3-[(2-nitrophenyl)amino]-L-alanine

HRID 1481890Notes

Reaction equation

[NH2:1][CH2:2][C@H:3]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:4]([OH:6])=[O:5].F[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23].C(=O)(O)[O-].[Na+].O>CN(C=O)C>[C:11]([O:10][C:8]([NH:7][C@@H:3]([CH2:2][NH:1][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[N+:22]([O-:24])=[O:23])[C:4]([OH:6])=[O:5])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of (S)-3-amino-2-tert-butoxycarbonylamino-propionic acid (Aldrich) (5 g, 24.48 mmol) in DMF (75 mL) was added 1-fluoro-2-nitro-benzene (2.92 mL, 26.93 mmol) and sodium bicarbonate (6.17 g, 73.44 mmol) at RT and the resulting mixture was heated at 80° C. for 18 h under nitrogen atmosphere. Water was added and the aqueous layer was washed with ethyl acetate. The pH of the aqueous solution was adjusted to 3 with the addition of 10% aqueous sodium bisulfate solution and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated under reduced pressure to give crude mass which was triturated with hexanes to afford (S)-2-tert-butoxycarbonylamino-3-(2-nitro-phenylamino)-propionic acid (5 g, 63%) as an orange yellow solid. LC-MS: 326.2 (M+H).

Workup

washthe aqueous layer was washed with ethyl acetate
additionThe pH of the aqueous solution was adjusted to 3 with the addition of 10% aqueous sodium bisulfate solution
extractionextracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated under reduced pressure
customto give crude mass which
customwas triturated with hexanes

Sources & evidence

ORD record: ord-1f92dc62a6f743649448964b64aaf13f
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409888B2

Reaction notes

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