Cesium carbonate → HCID 131719568, compound

HRID 264899Notes

Reaction equation

HRID 264899 reaction equation
[CH2:1]([NH:5][C:6](=[O:38])[C@H:7]([CH3:37])[CH2:8][C@H:9]([OH:36])[C@@H:10]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:11][C@@H:12]([CH:25]([CH3:27])[CH3:26])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[C:16]([OH:24])[CH:15]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:45]([O:47][C:48](=[O:51])[CH2:49]I)[CH3:46]>CC(C)=O>[CH2:1]([NH:5][C:6](=[O:38])[C@H:7]([CH3:37])[CH2:8][C@H:9]([OH:36])[C@@H:10]([NH:28][C:29]([O:31][C:32]([CH3:34])([CH3:33])[CH3:35])=[O:30])[CH2:11][C@@H:12]([CH:25]([CH3:26])[CH3:27])[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[C:16]([O:24][CH2:49][C:48]([O:47][CH2:45][CH3:46])=[O:51])[CH:15]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 12183Ethyl iodoacetateHCID 131719566HCID 131719566, compound

Product 1

HCID 131719568HCID 131719568, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 52 mg of N-tert-butoxycarbonyl-2(R)-methyl-4(S)-hydroxy-5(S)-amino-7(S)-isopropyl-8-(3-hydroxy-4-tert-butyl-phenyl)-octanoic acid (N-butyl)amide (Example 5a), 47.5 mg of caesium carbonate, 0.012 ml of iodoacetic acid ethyl ester and 5 ml of acetone is stirred for 3 hours under reflux and then concentrated by evaporation. The residue is partitioned between diethyl ether and water. The organic phases are dried and combined and then concentrated by evaporation, yielding the title compound in the form of the crude product: Rf (dichloromethane/diethyl ether=8:2)=0.28.

Workup

  1. temperatureunder reflux
  2. concentrationconcentrated by evaporation
  3. customThe residue is partitioned between diethyl ether and water
  4. customThe organic phases are dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6f5f1d23d90c4787bcc81e6f5e9e9cdc
Source dataset
uspto-grants-1997_07
Patent number
US05646143

Reaction notes

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