Sulfuric Acid → HCID 56640794, compound
Reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C@@H:20]2[CH2:25][CH2:24][C:23](=[N:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:22][NH:21]2)=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[BH4-].[Na+].C(=O)([O-])O.[Na+]>C(#N)C.O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18]([C@@H:20]2[CH2:25][CH2:24][C@@H:23]([NH:26][O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:22][NH:21]2)=[O:19])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- -10 °C
Procedure
To 4-[({(2S)-5-[(benzyloxy)imino]piperidin-2-yl}carbonyl)amino]piperidine-1-carboxylic acid benzyl ester (0.4641 g, 1.00 mmol), tetrahydrofuran (3.2 ml) and acetonitrile (0.8 ml) were added, and the obtained mixture was cooled down to −10° C. Sulfuric acid (0.588 g, 6.00 mmol) and subsequently sodium borohydride (0.113 g, 3.00 mmol) were added to the mixture, and after 21 hours of stirring, saturated sodium hydrogen carbonate aqueous solution (5 ml) was added. The reaction mixture was extracted with ethyl acetate (10 ml), and the extracted mixture was analyzed with high performance liquid chromatography to find that the extracted mixture contained 0.366 g of the title compound, and the reduction reaction proceeded with yield of 79%. The diastereo selectivity was (2S,5R)/(2S,5S)=87.3/12.7 (74.6% de).
Workup
- extractionThe reaction mixture was extracted with ethyl acetate (10 ml)
- customthe reduction reaction
Sources & evidence
- ORD record
- ord-01c53b20697f4d32b4ba8133e8122212
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096523B2
Reaction notes
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