Diazomethane → methyl(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoate

HRID 1180421Notes

Reaction equation

HRID 1180421 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.[N+](=[CH2:26])=[N-]>CO.C(OCC)C.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[O:9][C@@H:10]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:11]([O:13][CH3:26])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 9550DiazomethaneHCID 69470808(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid

Product 1

HCID 69469636methyl(2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2S)-2-{[(R)-(4-bromophenyl)(phenyl)methyl]oxy}-4-methylpentanoic acid from step 2 example 1, (2.5 g, 6.6 mmol) in methanol (25 mL) at 0° C. was added portionwise diazomethane in diethyl ether until the yellow color persisted. A few drops of acetic acid were then added to quench the excess diazomethane. The colorless solution was concentrated and then the volatiles were coevaporated twice with n-heptane. The oil was pumped on to remove the last traces of solvent.

Workup

  1. customto quench the excess diazomethane
  2. concentrationThe colorless solution was concentrated
  3. customto remove the last traces of solvent

Sources & evidence

ORD record
ord-2ab83d1ffcf44afc93354abb2b6faf93
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

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