Dimethyl acetylenedicarboxylate → HCID 59271860, compound

HRID 1893199Notes

Reaction equation

HRID 1893199 reaction equation
[NH2:1]/[C:2](=[N:19]\[OH:20])/[CH:3]([N:10]([CH3:18])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:4][CH2:5][CH2:6][CH:7]([OH:9])[CH3:8].[CH3:21][O:22][C:23]([C:25]#[C:26][C:27]([O:29][CH3:30])=[O:28])=[O:24]>CO>[NH2:1]/[C:2](=[N:19]\[O:20]/[C:25](=[CH:26]/[C:27]([O:29][CH3:30])=[O:28])/[C:23]([O:22][CH3:21])=[O:24])/[CH:3]([N:10]([C:11]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:17])[CH3:18])[CH2:4][CH2:5][CH2:6][CH:7]([OH:9])[CH3:8]

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 59271887HCID 59271887, compound

Product 1

HCID 59271860HCID 59271860, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-10 °C

Procedure

The tert-butyl {1-[(Z)-amino(hydroxyimino)methyl]-5-hydroxyhexyl}methylcarbamate (161 g, overweight) was dissolved in methanol (250 mL) and cooled to −10° C. DMAD (65 mL) was added dropwise without allowing the reaction temperature to rise above −5° C. then the reaction mixture was stored in a freezer at −10° C. for 2 days. The reaction mixture was then concentrated to dryness. It was azeotropically dried twice with toluene and dried in vacuo at 30° C. to constant weight to afford the title product: ES MS M+1=431.9.

Workup

  1. customto rise above −5° C.
  2. concentrationThe reaction mixture was then concentrated to dryness
  3. dry with materialIt was azeotropically dried twice with toluene
  4. customdried in vacuo at 30° C. to constant weight

Sources & evidence

ORD record
ord-f535b2b830d44b2e9730580bd151e943
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

Loading…