Triethylamine → HCID 58748281, compound

HRID 1162711Notes

Reaction equation

HRID 1162711 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:10][C@H:9]1[CH2:22][OH:23])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O.CCOC(C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH:13][C:14]([C:16]2[S:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[O:15])[CH2:10][C@H:9]1[CH:22]=[O:23])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 58748309HCID 58748309, compound

Product 1

HCID 58748281HCID 58748281, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Procedure

89.1 To a stirred, cooled (0° C.) solution of 1.48 g (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (example 17.1) in 30 ml CH2Cl2/DMSO 1:1 under an argon atmosphere were added 5.7 ml triethylamine and 3.92 g SO3-pyridine complex in one portion. The clear solution (slowly warming up to room temperature) was then stirred for 3 h. The mixture was diluted with EtOAc and washed with 1 N HCl. The aqueous phase was back extracted with EtOAc. The combined organics were washed with 1 N HCl, H2O and brine, dried over MgSO4, filtered and concentrated. The crude product was purified by chromatography (silica gel; cyclohexane/EtOAc 1:1) to give 985 mg (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-formyl-pyrrolidine-1-carboxylic acid tert-butyl ester as white amorphous solid. MS 359.0 ([M+H]+)

Workup

  1. washwashed with 1 N HCl
  2. extractionThe aqueous phase was back extracted with EtOAc
  3. washThe combined organics were washed with 1 N HCl, H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (silica gel; cyclohexane/EtOAc 1:1)

Sources & evidence

ORD record
ord-24aff0c881d942188f82957e3a1376cf
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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