Diazomethane → HCID 25119717, compound

HRID 1798463Notes

Reaction equation

HRID 1798463 reaction equation
[CH:1]1([N:4]([CH2:32][C:33]2[CH:34]=[C:35]([CH:44]=[C:45]([CH2:47][CH2:48][CH2:49][O:50][CH3:51])[CH:46]=2)[O:36][CH2:37][C@@H:38]2[CH2:40][C@H:39]2[C:41]([OH:43])=[O:42])[C:5]([C@@H:7]2[C@@H:12]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]4[C:28]([Cl:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[Cl:31])=[CH:15][CH:14]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1.[N+](=[CH2:54])=[N-]>CCOCC>[CH:1]1([N:4]([CH2:32][C:33]2[CH:34]=[C:35]([CH:44]=[C:45]([CH2:47][CH2:48][CH2:49][O:50][CH3:51])[CH:46]=2)[O:36][CH2:37][C@@H:38]2[CH2:40][C@H:39]2[C:41]([O:43][CH3:54])=[O:42])[C:5]([C@@H:7]2[C@@H:12]([C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][O:22][C:23]4[C:28]([Cl:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=4[Cl:31])=[CH:17][CH:18]=3)[CH2:11][CH2:10][NH:9][CH2:8]2)=[O:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 25119712HCID 25119712, compound

Product 1

HCID 25119717HCID 25119717, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (1R,2R)-2-{[3-({cyclopropyl[((3R,4S)-4-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}piperidin-3-yl)carbonyl]amino}methyl)-5-(3-methoxypropyl)phenoxy]methyl}cyclopropanecarboxylic acid (1 eq., neutral form) from Example 2 was added a solution of diazomethane in ether until a faint yellow color persisted. The solvent was evaporated by a stream of nitrogen gas. The residue was purified by flash column chromatography (SiO2, 10% MeOH in DCM plus 1% aqueous NH4OH) afford the title compound as a colorless oil.

Workup

  1. customThe solvent was evaporated by a stream of nitrogen gas
  2. customThe residue was purified by flash column chromatography (SiO2, 10% MeOH in DCM plus 1% aqueous NH4OH)

Sources & evidence

ORD record
ord-bd7c93d5a9af43ea9182d90a5a410840
Source dataset
uspto-grants-2013_01
Patent number
US08343968B2

Reaction notes

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