Guaiacol → (2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(2-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 732609Notes

Reaction equation

HRID 732609 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:15]([O:19][C:20]([N:22]1[CH2:26][C@@H:25]([OH:27])[CH2:24][C@@H:23]1[C@H:28]1[O:32][C:31]([CH3:34])([CH3:33])[N:30]([C:35](=[O:37])[CH3:36])[C@H:29]1[CH2:38][C:39]1[CH:44]=[C:43]([F:45])[CH:42]=[C:41]([F:46])[CH:40]=1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[CH3:47][O:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][C:50]=1O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:15]([O:19][C:20]([N:22]1[CH2:26][C@H:25]([O:27][C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][C:49]=2[O:48][CH3:47])[CH2:24][C@@H:23]1[C@H:28]1[O:32][C:31]([CH3:33])([CH3:34])[N:30]([C:35](=[O:37])[CH3:36])[C@H:29]1[CH2:38][C:39]1[CH:40]=[C:41]([F:46])[CH:42]=[C:43]([F:45])[CH:44]=1)=[O:21])([CH3:16])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 460GuaiacolHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 68814265(2R,4S)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 68817598(2R,4R)-2-[(4S,5S)-3-Acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-(2-methoxy-phenoxy)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add dropwise diisopropyl azodicarboxylate (0.065 mL, 0.327 mmol) to a solution of (2R,4S)-2-[(4S,5S)-3-acetyl-4-(3,5-difluoro-benzyl)-2,2-dimethyl-oxazolidin-5-yl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.099 g, 0.218 mmol), 2-methoxy phenol (0.036 mL, 0.327 mmol) and triphenylphosphine (0.086 g, 0.327 mmol) in tetrahydrofuran (1.5 mL). Stir 18 hours. Purify reaction mixture on silica gel with ethyl acetate/hexane mixtures to give the desired compound as a foam (0.064 g, 53%). MS(ES): m/z=561 [M+H].

Workup

  1. customPurify
  2. customreaction mixture on silica gel with ethyl acetate/hexane

Sources & evidence

ORD record
ord-018b90170c6345e9bf6c6861078a6d6b
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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