Ethyl orthoformate → HCID 68602981, compound

HRID 2090218Notes

Reaction equation

HRID 2090218 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:5]([CH3:32])=[CH:6][NH:7][C:8](=[O:31])[C:9]=2[CH:10]([C:19]2[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=2[O:27][C:26]([CH3:29])=[CH:25][C:24]3=[O:30])[C:11]=1[C:12]([O:14][CH2:15][CH2:16][C:17]#[N:18])=[O:13].C(OCC)(OCC)O[CH2:35][CH3:36]>CN(C=O)C.S(=O)(=O)(O)O>[CH2:35]([O:31][C:8]1[N:7]=[CH:6][C:5]([CH3:32])=[C:4]2[C:9]=1[CH:10]([C:19]1[CH:20]=[CH:21][CH:22]=[C:23]3[C:28]=1[O:27][C:26]([CH3:29])=[CH:25][C:24]3=[O:30])[C:11]([C:12]([O:14][CH2:15][CH2:16][C:17]#[N:18])=[O:13])=[C:2]([CH3:1])[NH:3]2)[CH3:36]

Participants

5

Reactant 2

HCID 31214Ethyl orthoformateHCID 68599190HCID 68599190, compound

Product 1

HCID 68602981HCID 68602981, compound

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

1.20 g (2.78 mmol) of the compound from Example 39A and 9.25 ml (55.6 mmol) of triethyl orthoformate are taken up in 30 ml of dry DMF and heated to 130° C., and 5 drops of concentrated sulfuric acid are added. After 2 h, an HPLC check shows complete conversion. After cooling, the volatile components are removed in a rotary evaporator, and the crude product is purified by MPLC (Biotage cartridge 40 M, eluent: isohexane/ethyl acetate 1:2). 640 mg (50% of theory) of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe volatile components are removed in a rotary evaporator
  3. customthe crude product is purified by MPLC (Biotage cartridge 40 M, eluent: isohexane/ethyl acetate 1:2)

Sources & evidence

ORD record
ord-0da98c2f74824cb2886b4f881dbfa25e
Source dataset
uspto-grants-2013_05
Patent number
US08436180B2

Reaction notes

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