Trimethylsilyldiazomethane → HCID 69732768, compound

HRID 896879Notes

Reaction equation

HRID 896879 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:18][C@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([S:29][C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=3)[C:33]([OH:35])=[O:34])[CH:25]=2)[O:20]1)[CH2:9][C@H:10]([OH:17])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:39][Si](C=[N+]=[N-])(C)C>CO.C(OCC)(=O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([CH2:18][C@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[C:24]([S:29][C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=3)[C:33]([O:35][CH3:39])=[O:34])[CH:25]=2)[O:20]1)[CH2:9][C@H:10]([OH:17])[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 69732470HCID 69732470, compound

Product 1

HCID 69732768HCID 69732768, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21584119Ethylacetate methanolSolvent

Procedure

To 650 mg (1.25 mmol) of 3-{[(2R)-2-({(tert-butoxycarbonyl)[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino}methyl)-3,4-dihydro-2H-chromen-6-yl]sulfanyl}benzoic acid (Example 173) dissolved in 10 mL 1:1 methanol/ethyl acetate, was added 3 mL of 2M trimethylsilyl diazomethane dropwise. The resulting solution was then allowed to stir at room temperature for 16 hours. The solution was then diluted with ethyl acetate, washed with water and brine, and concentrated in vacuo. The crude mixture was purified by Biotage with 75% ethyl acetate/hexanes to obtain 223 mg (33% yield) of product; MH+ 551.2.

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated in vacuo
  3. customThe crude mixture was purified by Biotage with 75% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-dc3755b276114d81b0ac64b02579f368
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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