Methanol → HCID 10237195, compound

HRID 1070896Notes

Reaction equation

HRID 1070896 reaction equation
[N+](=[CH2:3])=[N-].C(OCC)C.[C:9]([C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:32])[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[C:29]([OH:31])=[O:30])=[O:23])(O)=[O:10].[CH3:33][OH:34]>O1CCCC1>[CH3:33][O:34][C:9]([C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[C:17](=[O:32])[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([N:24]1[CH2:28][CH2:27][CH2:26][C@@H:25]1[C:29]([O:31][CH3:3])=[O:30])=[O:23])=[O:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 3283Diethyl EtherHCID 9550DiazomethaneHCID 125516Miridesap

Product 1

HCID 10237195HCID 10237195, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of diazomethane in diethylether (˜6 mmol) was added to a solution of 500 mg (1.5 mmol) (R)-1-[6-[(R)-2-carboxy-pyrrolidin-1-yl]-6-oxo-hexanoyl]-pyrrolidine-2-carboxylic acid in 10 ml tetrahydrofuran. After stirring overnight methanol was added and the solvents were evaporated. The residue was taken up in dichloromethane, extracted with brine and dried with sodium sulfate. After separation from the solvent 400 mg (72%) (R)-1-{6-[(R) -2-methoxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid methyl ester were obtained as a light yellow oil, MS m/e (%): 369 (M+H+, 100).

Workup

  1. additionwas added
  2. customthe solvents were evaporated
  3. extractionextracted with brine
  4. dry with materialdried with sodium sulfate
  5. customAfter separation from the solvent 400 mg (72%) (R)-1-{6-[(R) -2-methoxycarbonyl-pyrrolidin-1-yl]-6-oxo-hexanoyl}-pyrrolidine-2-carboxylic acid methyl ester
  6. customwere obtained as a light yellow oil, MS m/e (%)

Sources & evidence

ORD record
ord-41614dc46b954e06ae130b5b54701c64
Source dataset
uspto-grants-2005_06
Patent number
US06903129B2

Reaction notes

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