Triethylamine → HCID 59520050, compound

HRID 1162706Notes

Reaction equation

HRID 1162706 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[C@H:10]([CH2:14][NH:15][C:16]([C:18]2[S:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=[O:13])[C@H:10]([CH2:14][NH:15][C:16]([C:18]2[S:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[O:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 58748178HCID 58748178, compound

Product 1

HCID 59520050HCID 59520050, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

81.1 To a solution of (3R,4S)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (600 mg, prepared according to example 79.5) in 10 ml of CH2Cl2 was added at 5° C. 2.30 ml of NEt3 and 1.59 g of SO3-pyridine complex, the solution was warmed to 22° C. and stirring was continued for 3 h. The mixture was washed with aqueous NH4Cl, the organic layer was dried and evaporated. The residue was chromatographed on silica (heptane/AcOEt, 2:1) to give 435 mg of (R)-3-{[(5-chloro-thiophene-2-carbonyl)-amino]-methyl}-4-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester. Pale yellow solid. MS 303.0 ([M-isobutene+H]+)

Workup

  1. washThe mixture was washed with aqueous NH4Cl
  2. customthe organic layer was dried
  3. customevaporated
  4. customThe residue was chromatographed on silica (heptane/AcOEt, 2:1)

Sources & evidence

ORD record
ord-736e13bb31b84467be1bfd847f233bee
Source dataset
uspto-grants-2010_10
Patent number
US07820699B2

Reaction notes

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