Benzene, 2-fluoro-4-methyl-1-nitro- → (2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyric acid

HRID 1055373Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[C:26]1C=C(C)C=CC=1[N+]([O-])=O>>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([O:14][C:15]1[CH:20]=[C:19]([CH3:21])[CH:18]=[CH:17][C:16]=1[N+:22]([O-:24])=[O:23])[CH3:26])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 67966Benzene, 2-fluoro-4-methyl-1-nitro-

HCID 67076916(S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid

Product 1

HCID 90036984(2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyric acidYield 53.6%

Conditions

Temperature: 0 °C

Procedure

In a similar manner to that described for the preparation of (S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid except the reaction mixture was stirred at 0° C. for 4 h, (2S,3S)-2-(tert-butoxycarbonylamino)-3-hydroxybutanoic acid DCHA (2.0 g, 5.00 mmol) and 2-fluoro-4-methyl-1-nitrobenzene (1.55 g, 9.99 mmol) were converted to (2S,3S)-2-tert-butoxycarbonylamino-3-(5-methyl-2-nitro-phenoxy)-butyric acid (0.95 g, 53.6% yield).

Sources & evidence

ORD record: ord-9627bb1260264296ac50b46695c1755c
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09394263B2

Reaction notes

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