Hydrochloric Acid → HCID 131714701, compound

HRID 1981664Notes

Reaction equation

HRID 1981664 reaction equation
[N:1](OCC(C)C)=[O:2].[CH2:8]([N:13]([C@:20]1([OH:35])[C@H:26]([OH:27])[C@@H:25]([CH2:28][OH:29])[O:24][C@:22]([CH2:30][CH:31]([CH3:33])[CH3:32])([OH:23])[C@@H:21]1[OH:34])[C:14](=[O:19])[NH:15][CH2:16][CH2:17][Cl:18])[CH2:9][CH:10]([CH3:12])[CH3:11].O1CCCC1.Cl>C(O)C>[CH2:8]([N:13]([C@:20]1([OH:35])[C@H:26]([OH:27])[C@@H:25]([CH2:28][OH:29])[O:24][C@:22]([CH2:30][CH:31]([CH3:33])[CH3:32])([OH:23])[C@@H:21]1[OH:34])[C:14](=[O:19])[N:15]([CH2:16][CH2:17][Cl:18])[N:1]=[O:2])[CH2:9][CH:10]([CH3:11])[CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 10958Isobutyl nitriteHCID 131714702HCID 131714702, compound

Product 1

HCID 131714701HCID 131714701, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Isobutyl nitrite (3.5 ml) was dropped into a solution of 3-isopentyl-3-(isobutyl α-D-glucopyranose-3-yl)-1-(2-chloroethyl)urea (3.48 g, 8.47 mmol) in a mixture of ethanol (50 ml), tetrahydrofuran (150 ml), and 2N hydrochloric acid (30 ml) with well stirring at 0° to 5° C. Thereafter, 2.51 g of 3-isopentyl-3-(isobutyl α-D-glucopyranose-3-yl)-1-(2-chloroethyl)-1-nitrosourea was obtained by the same operations of Example 63(2); yield 67.3%, m.p. 69°-71° C., [α]D20 +45.8° (C 1.0, methanol).

Sources & evidence

ORD record
ord-821fff362d164ee69cdce4e60cb3ecee
Source dataset
uspto-grants-1986_06
Patent number
US04593090

Reaction notes

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