Butylamine → N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

HRID 877951Notes

Reaction equation

HRID 877951 reaction equation
[OH:1][CH2:2][C@H:3]1[O:8][C:7]([CH3:10])([CH3:9])[O:6][C@@H:5]([CH2:11][C:12]([O:14]C(C)(C)C)=O)[CH2:4]1.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22]>CO>[CH2:19]([NH:23][C:12](=[O:14])[CH2:11][C@H:5]1[CH2:4][C@@H:3]([CH2:2][OH:1])[O:8][C:7]([CH3:9])([CH3:10])[O:6]1)[CH2:20][CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 8007ButylamineHCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Product 1

HCID 53339170N-butyl-2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

Mixture of tert-butyl 2-((4R,6S)-6-(hydroxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (50 grams), methanol (300 ml) and n-butyl amine (200 ml) was heated to 60-70° C. under nitrogen pressure and stirred. After the completion of the reaction, distilled off the reaction mixture completely followed by co-distillation with methylene chloride at below 55° C. Methylene chloride (500 ml) was added to the obtained residue at 25-30° C. and stirred for 15 minutes. The unwanted solid was filtered off and the filtrate was distilled off under reduced pressure to get the title compound.

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled off the reaction mixture
  3. customcompletely followed by co-distillation with methylene chloride at below 55° C
  4. additionMethylene chloride (500 ml) was added to the obtained residue at 25-30° C.
  5. stirringstirred for 15 minutes
  6. filtrationThe unwanted solid was filtered off
  7. distillationthe filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d2d5b4cdaaf74778a8698f5a8416efec
Source dataset
uspto-grants-2015_03
Patent number
US08987444B2

Reaction notes

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