Water → HCID 42643385, compound

HRID 1875355Notes

Reaction equation

HRID 1875355 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:12]([CH2:22][OH:23])[CH2:11]2)=[O:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].O>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][C@H:10]2[CH2:14][N:13]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C@H:12]([CH2:22][O:23][S:32]([CH3:31])(=[O:34])=[O:33])[CH2:11]2)=[O:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58748309HCID 58748309, compound

Product 1

HCID 42643385HCID 42643385, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

278.0 mg (0.8 mmol) tert. Butyl (2S,4R)-4-[(5-chloro-thiophene-2-carbonyl)-amino]-2-hydroxymethyl-pyrrolidine-1-carboxylate are dissolved in 6 ml DCM and combined with 216 μl (1.5 mmol) triethylamine. 89 μl (1.2 mmol) methanesulphonic acid chloride are added while cooling with the ice bath. The reaction mixture is heated to RT and stirred for two hours. Then it is mixed with water and extracted three times with ethyl acetate. The combined organic phases are dried on sodium sulphate, filtered and evaporated down i. vac.

Workup

  1. extractionextracted three times with ethyl acetate
  2. customThe combined organic phases are dried on sodium sulphate
  3. filtrationfiltered
  4. customevaporated down i

Sources & evidence

ORD record
ord-4bbec9dea4934dc088ee22b2627178df
Source dataset
uspto-grants-2012_11
Patent number
US08309542B2

Reaction notes

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