Diisopropylethylamine → HCID 17751325, compound

HRID 643884Notes

Reaction equation

HRID 643884 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[CH2:16][C:15](=[O:17])[NH:14][S:13]1(=[O:19])=[O:18])[CH:8]=[C:7]([CH2:20][CH2:21][CH2:22][C:23]([CH3:28])([CH3:27])[C:24]([OH:26])=[O:25])[CH:6]=[CH:5]2.[CH3:29]CN(C(C)C)C(C)C.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:29][O:25][C:24](=[O:26])[C:23]([CH3:28])([CH3:27])[CH2:22][CH2:21][CH2:20][C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][C:11]([N:12]3[CH2:16][C:15](=[O:17])[NH:14][S:13]3(=[O:19])=[O:18])=[C:2]([OH:1])[CH:3]=2)[CH:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 66750756HCID 66750756, compound

Product 1

HCID 17751325HCID 17751325, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-[6-hydroxy-7-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-naphthalen-2-yl]-2,2-dimethylpentanoic acid (Example LCE840, 63 mg, 0.13 mmol) in MeOH at 0° C. is added DIEA (0.032 mL, 0.13 mmol). After is stirred for 2 min, trimethylsilyldiazomethane (2M, 0:07 mL) is added drop wise. The reaction mixture is stirred for 15 min and concentrated give the title compound: Retention time=1.28 min (Method A); (M−H)−=419.

Workup

  1. stirringThe reaction mixture is stirred for 15 min
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-f77dbae1de60423fb3d4815368d7b003
Source dataset
uspto-grants-2010_04
Patent number
US07700633B2

Reaction notes

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