Hydrochloric Acid → (2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

HRID 458333Notes

Reaction equation

HRID 458333 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([S:7]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)(=[O:9])=[O:8])[C@H:4]([C:20]([OH:22])=[O:21])[CH2:3]1.Cl.[CH3:24]O>>[CH3:24][O:21][C:20]([C@@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][N:5]1[S:7]([C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=1)(=[O:8])=[O:9])=[O:22]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 6363699(2s,4r)-4-Hydroxy-1-(naphthalene-2-sulfonyl)pyrrolidine-2-carboxylic acid

Product 1

HCID 7987003(2S,4R)-4-Hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Procedure

38.97 g (121.4 mmol) (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid were dissolved in 97 ml MeOH and 64.5 ml 1.75 M (112.8 mmol) HCl in MeOH were added and the solution heated to reflux for 3 h and concentrated. Trituration with hexane yielded 41.4 g (quant.) (2S,4R)-4-hydroxy-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as brown solid, MS: 335 (MH+).

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-afb69d3a06394807a1e020cc4ea3b7f9
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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