N-Boc-4-oxo-L-proline
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N-Boc-4-oxo-L-proline

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A reagent used in the syntheisis of benzidine and diaminofluorene prolinamide derivatives which are highly potent HCV inhibitors.

Category
BOC-Amino Acids
Catalog number
BAT-000782
CAS number
84348-37-8
Molecular Formula
C10H15NO5
Molecular Weight
229.23
N-Boc-4-oxo-L-proline
IUPAC Name
(2S)-1-[(2-methylpropan-2-yl)oxycarbonyl]-4-oxopyrrolidine-2-carboxylic acid
Synonyms
Boc-4-oxo-Pro-OH; (S)-1-(Tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid; N-t-boc-4-oxo-L-proline; N-tert-Boc-4-oxo-L-proline
Purity
98%
Melting Point
160 °C (dec.)
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H15NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h7H,4-5H2,1-3H3,(H,13,14)/t7-/m0/s1
InChI Key
CKYGSXRXTIKGAJ-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CC(=O)CC1C(=O)O
1.Practical synthesis of Boc-protected cis-4-trifluoromethyl and cis-4-difluoromethyl-L- prolines.
Qiu XL1, Qing FL. J Org Chem. 2002 Oct 4;67(20):7162-4.
A short, efficient, and diastereomerically pure synthesis of N-Boc-cis-4-trifluoromethyl-L-proline (7) and N-Boc-cis-4-difluoromethyl-L-proline (9) from N-Boc-4-oxo-L-proline (4) is described. The reaction of 4 with Me(3)SiCF(3) and the conversion of the carbonyl group of 4 into the difluoromethylene group are the key steps for the synthesis of 7 and 9, respectively.
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